Substituted cyclopentene derivatives and method for preparing the same

A method for preparing a halogenated substituted cyclopentene derivative of the formula (I):

• 74
• wherein R, X1, X3, and W are as defined below,
• said method comprising the step of reacting a substituted cyclopentane derivative of the formula (II):
• 75
• wherein R is a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, aralkyl radical having 7 to 19 carbon atoms, aryl radical having 6 to 12 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, alkylthio radical having 1 to 6 carbon atoms or alkenylthio radical having 2 to 6 carbon atoms;
• X1 is (α-OZa, β-H) or (α-H, β-OZa) , X3 is (α-OZd, β-H), (α-H, β-OZd) or oxygen atom, Y is (α-OZc, β-H) or (α-H, β-OZc), and each of Za, Zc and Zd, which may be the same or different, is a hydrogen atom or a protective radical for a hydroxyl radical, with a halide of the formula (III):
• M1Wh (III)
• wherein M1 is a metal atom selected from the group consisting of an alkali metal, alkaline earth metal, first transition metal, Al, Zr, and Ce, or quaternary ammonium, W is a halogen atom, and h representative of the valence of said metal or quaternary ammonium is an integer of 1 to 4, or a hydrate thereof in the presence or absence of a Lewis acid.

A method for preparing a substituted cyclopentene derivative of the formula (V):

• 76
• wherein R, X1, X3, U, R5, R6, R7, R8, X2, m, n, p, q, and Z1 are as defined below,
• said method characterized by comprising the step of reacting a halogenated substituted cyclopentene derivative of the formula (I):
• 77
• wherein R is a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, aralkyl radical having 7 to 19 carbon atoms, aryl radical having 6 to 12 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, alkylthio radical having 1 to 6 carbon atoms or alkenylthio radical having 2 to 6 carbon atoms;
• X1 is (α-OZa, β-H) or (α-H, β-OZa) X3 is (α-OZd, β-H), (α-H, β-OZd) or oxygen atom, each of Za and Zd, which may be the same or different, is a hydrogen atom or a protective radical for a hydroxyl radical;
• and W is a halogen atom with a compound of the formula (IV):
• M2Um(CR5R6)nX2p(CR7R8)qZ1 (IV)
• wherein M2 is a substituted borane radical, substituted aluminum radical, substituted zirconium radical or substituted stannyl radical each having a hydrogen atom, alkyl radical having 1 to 9 carbon atoms, cycloalkyl radical having 3 to 12 carbon atoms, aralkyl radical having 7 to 10 carbon atoms, aryl radical having 6 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, dialkoxy radical having 2 to 12 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, substituted phenoxy radical, a cyclopentadienyl radical or halogen atom substituent;
• U is a radical selected from the group consisting of CR1R2CR3R4, CR1═CR3, C≡C, and phenylene wherein R1 is a hydrogen atom, alkyl radical having 1 to 9 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, aralkyl radical having 7 to 10 carbon atoms, aryl radical having 6 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, halogen atom, substituted silyl radical represented by SiR9R10R11 or substituted stannyl radical represented by SnR14R15R16 wherein R9, R10 and R11 are independently selected from the group consisting of a hydrogen atom, chlorine atom, fluorine atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, phenyl radical, tolyl radical, and benzyl radical, R14, R15 and R16 are independently selected from the group consisting of a hydrogen atom, chlorine atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, phenyl radical, tolyl radical, and benzyl radical;
• R2, R3, and R4 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms;
• m is an integer of 0 to 6;
• R5, R6, R7, and R8 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxycarbonyl radical, and alkenyloxycarbonyl radical;
• X2 is CR12═CR13, C≡C, phenylene radical, carbonyl radical, oxygen atom or sulfur atom wherein R12 and R13 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms;
• p is an integer of 0 or 1, each of n and q is an integer of 0 to 5;
• and
• Z1 is a hydrogen atom, COORy, CN, OH, OCORz, CONRbRc or NRdRe wherein Ry and Rz are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rb and Rc are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rd and Re are independently selected from the group consisting of a hydrogen atom, benzyl radical, phenyl radical, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, in the presence or absence of a metal catalyst.

A compound of the formula (IV):

• M2Um(CR5R6)nX2p(CR7R8)qZ1 (IV)
• wherein M2 is a substituted borane radical, substituted aluminum radical, substituted zirconium radical or substituted stannyl radical each having a hydrogen atom, alkyl radical having 1 to 9 carbon atoms, cycloalkyl radical having 3 to 12 carbon atoms, aralkyl radical having 7 to 10 carbon atoms, aryl radical having 6 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, dialkoxy radical having 2 to 12 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, substituted phenoxy radical, a cyclopentadienyl radical or halogen atom substituent;
• U is a radical selected from the group consisting of CR1R2CR3R4, CR1═CR3, C≡C, and phenylene wherein R1 is a hydrogen atom, alkyl radical having 1 to 9 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, aralkyl radical having 7 to 10 carbon atoms, aryl radical having 6 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, halogen atom, substituted silyl radical represented by SiR9R10R11 or substituted stannyl radical represented by SnR14R15R16 wherein R9, R10 and R11 are independently selected from the group consisting of a hydrogen atom, chlorine atom, fluorine atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, phenyl radical, tolyl radical, and benzyl radical, R14, R15 and R16 are independently selected from the group consisting of a hydrogen atom, chlorine atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, phenyl radical, tolyl radical, and benzyl radical;
• R2, R3, and R4 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms;
• m is an integer of 0 to 6;
• R5, R6, R7, and R8 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxycarbonyl radical, and alkenyloxycarbonyl radical;
• X2 is CR12═CR13, C≡C, phenylene radical, carbonyl radical, oxygen atom or sulfur atom wherein R12 and R13 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms;
• p is an integer of 0 or 1, each of n and q is an integer of 0 to 5;
• and
• Z1 is a hydrogen atom, COORy, CN, OH, OCORz, CONRbRc or NRdRe wherein Ry and Rz are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rb and Rc are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rd and Re are independently selected from the group consisting of a hydrogen atom, benzyl radical, phenyl radical, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms.

A compound of the formula (V):

• 78
• wherein R is a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, aralkyl radical having 7 to 19 carbon atoms, aryl radical having 6 to 12 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, alkylthio radical having 1 to 6 carbon atoms or alkenylthio radical having 2 to 6 carbon atoms;
• X1 is (α-OZa, β-H) or (α-H, β-OZa), X3 is (α-OZd, β-H), (α-H, β-OZd) or oxygen atom, each of Za and Zd, which may be the same or different, is a hydrogen atom or a protective radical for a hydroxyl radical;
• U is a radical selected from the group consisting of CR1R2CR3R4, CR1═CR3, C≡C, and phenylene wherein R1 is a hydrogen atom, alkyl radical having 1 to 9 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, aralkyl radical having 7 to 10 carbon atoms, aryl radical having 5 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, halogen atom, substituted silyl radical represented by SiR9R10R11 or substituted stannyl radical represented by SnR14R15R16 wherein R9, R10 and R11 are independently selected from the group consisting of a hydrogen atom, chlorine atom, fluorine atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, phenyl radical, tolyl radical, and benzyl radical, R14, R15 and R16 are independently selected from the group consisting of a hydrogen atom, chlorine atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, phenyl radical, tolyl radical, and benzyl radical;
• R2, R3, and R4 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms;
• m is an integer of 0 to 6;
• R5, R6, R7, and R8 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxycarbonyl radical, and alkenyloxycarbonyl radical;
• X2 is CR12═CR13, C≡C, phenylene radical, carbonyl radical, oxygen atom or sulfur atom wherein R12 and R13 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms;
• p is an integer of 0 or 1, each of n and q is an integer of 0 to 5;
• and
• Z1 is a hydrogen atom, COORy, CN, OH, OCORz, CONRbRc or NRdRe wherein Ry and Rz are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rb and Rc are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rd and Re are independently selected from the group consisting of a hydrogen atom, benzyl radical, phenyl radical, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms.

A substituted cyclopentene derivative of the formula (VII):

• 79
• wherein R is a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, aralkyl radical having 7 to 19 carbon atoms, aryl radical having 6 to 12 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, alkylthio radical having 1 to 6 carbon atoms or alkenylthio radical having 2 to 6 carbon atoms;
• X1 is (α-OZa, β-H) or (α-H, β-OZa), X3 is (α-OZd, β-H), (α-H, β-OZd) or oxygen atom, each of Za and Zd, which may be the same or different, is a hydrogen atom or a protective radical for a hydroxyl radical;
• R1 is a hydrogen atom, alkyl radical having 1 to 9 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, aralkyl radical having 7 to 10 carbon atoms, aryl radical having 6 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, halogen atom, substituted silyl radical represented by SiR9R10R11 or substituted stannyl radical represented by SnR 14R15R16 wherein R9, R10 and R11 are independently selected from the group consisting of a hydrogen atom, chlorine atom, fluorine atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, phenyl radical, tolyl radical, and benzyl radical, R14, R15 and R16 are independently selected from the group consisting of a hydrogen atom, chlorine atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, phenyl radical, tolyl radical, and benzyl radical;
• R3 is a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms or cycloalkyl radical having 3 to 8 carbon atoms;
• R5, R6, R7, and R8 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxycarbonyl radical, and alkenyloxycarbonyl radical;
• X2 is CR12═CR13, C≡C, phenylene radical, carbonyl radical, oxygen atom or sulfur atom wherein R12 and R13 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms;
• p is an integer of 0 or 1, each of n and q is an integer of 0 to 5;
• and
• Z1 is a hydrogen atom, COORy, CN, OR, OCORz, CONRbRc or NRdRe wherein Ry and Rz are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rb and Rc are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rd and Re are independently selected from the group consisting of a hydrogen atom, benzyl radical, phenyl radical, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms.

A method for preparing a substituted cyclopentene derivative of the formula (VII):

• 80
• wherein R, X1, X3, R1, R3, R5, R6, R7, R8, X2, n, p, q, and Z1 are as defined below,
• said method characterized by comprising the step of oxidizing with an oxidizing agent such as peroxides a substituted cyclopentene derivative of the formula (VI):
• 81
• wherein R is a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, aralkyl radical having 7 to 19 carbon atoms, aryl radical having 6 to 12 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, alkylthio radical having 1 to 6 carbon atoms or alkenylthio radical having 2 to 6 carbon atoms;
• X1 is (α-OZa, β-H) or (α-H, β-OZa) , X3 is (α-OZd, β-H), (α-H, β-OZd) or oxygen atom, each of Za and Zd, which may be the same or different, is a hydrogen atom or a protective radical for a hydroxyl radical;
• R1 is a hydrogen atom, alkyl radical having 1 to 9 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, aralkyl radical having 7 to 10 carbon atoms, aryl radical having 6 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, halogen atom, substituted silyl radical represented by SiR9R10R11 or substituted stannyl radical represented by SnR14R15R16 wherein R9, R10 and R11 are independently selected from the group consisting of a hydrogen atom, chlorine atom, fluorine atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, phenyl radical, tolyl radical, and benzyl radical, R14, R15 and R16 are independently selected from the group consisting of a hydrogen atom, chlorine atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, phenyl radical, tolyl radical, and benzyl radical;
• R3 is a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms or cycloalkyl radical having 3 to 8 carbon atoms;
• R5, R6, R7, and R8 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxycarbonyl radical, and alkenyloxycarbonyl radical;
• X2 is CR12═CR13, C≡C, phenylene radical, carbonyl radical, oxygen atom or sulfur atom wherein R12 and R13 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms;
• p is an integer of 0 or 1, each of n and q is an integer of 0 to 5;
• and
• Z1 is a hydrogen atom, COORy, CN, OH, OCORz, CONRbRc or NRdRe wherein Ry and Rz are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rb and Rc are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rd and Re are independently selected from the group consisting of a hydrogen atom, benzyl radical, phenyl radical, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms.

A method for preparing a substituted cyclopentene derivative of the formula (IX):

• 82
• wherein R, X1, X3, R3, R5, R6, R7, R8, X2, n, p, q, and Z1 are as defined below,
• said method characterized by comprising the step of subjecting to acidolysis a substituted cyclopentene derivative of the formula (VIII):
• 83
• wherein R is a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, aralkyl radical having 7 to 19 carbon atoms, aryl radical having 6 to 12 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, alkylthio radical having 1 to 6 carbon atoms or alkenylthio radical having 2 to 6 carbon atoms;
• X1 is (α-OZa, β-H) or (α-H, β-OZa), X3 is (α-OZd, β-H), (α-H, β-OZd) or oxygen atom, each of Za and Zd, which may be the same or different, is a hydrogen atom or a protective radical for a hydroxyl radical;
• R9, R10 and R11 are independently selected from the group consisting of a hydrogen atom, chlorine atom, fluorine atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxy radical having 1 to 6 carbon atoms, alkenyloxy radical having 2 to 6 carbon atoms, phenyl radical, tolyl radical, and benzyl radical;
• R5, R6, R7, and R8 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, cycloalkyl radical having 3 to 8 carbon atoms, alkoxycarbonyl radical, and alkenyloxycarbonyl radical;
• X2 is CR12═CR13, C≡C, phenylene radical, carbonyl radical, oxygen atom or sulfur atom wherein R12 and R13 are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms;
• p is an integer of 0 or 1, each of n and q is an integer of 0 to 5;
• and
• Z1 is a hydrogen atom, COORy, CN, OH, OCORz, CONRbRc or NRdRe wherein Ry and Rz are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rb and Rc are independently selected from the group consisting of a hydrogen atom, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms, Rd and Re are independently selected from the group consisting of a hydrogen atom, benzyl radical, phenyl radical, alkyl radical having 1 to 6 carbon atoms, alkenyl radical having 2 to 6 carbon atoms, alkynyl radical having 2 to 6 carbon atoms, and cycloalkyl radical having 3 to 8 carbon atoms.