Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins
AssigneeUniversity of Pittsburgh
InventorsDennis P. Curran, Ana E. Gabarda
Life of this patent
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Abstract
A method of synthesizing a compound having the formula: from a compound having the formula: wherein R1 is hydrogen, fluorine, chlorine or SiR5R6R7, wherein R5, R6, and R7 are independently the same or different an alkyl group or an aryl group, R2 is an alkyl group, R3 is a protecting group, R4 is an alkyl group, an allyl group, a propargyl group —CO2H, or a benzyl group, R8 is —CO2R10, wherein R10 is an alkyl group or an aryl group, X1 is OH and X2 is H, includes the step of exposing compound (III) to at least one of an organic acid or an inorganic acid. A compound has the general formula (III).
Claims23
A compound having the formula:
- wherein R1 is fluorine, chlorine or SiR5R6R7, wherein R5, R6, and R7 are independently the same or different an alkyl group or an aryl group, R2 is an alkyl group, R3 is a protecting group, R4 is an alkyl group, an allyl group, a propargyl group or a beuzyl group, R8 is —CHO, —CH2OH, —CH2OR9, wherein R9 is a protecting group, —CO2H, or —CO2R10 wherein R10, is an alkyl group or an aryl group, and X1 is OH, X2 is H or OH, or X1 and X2 together are O, OS(O)O or OS(O2)O.
A compound having the formula:
- wherein R1 is hydrogen, fluorine, chlorine or SiR5R6R7, wherein R5, R6, and R7 are independently the same or different an alkyl group or an aryl group, R2 is an alkyl group, R3 is a protecting group, R4 is an alkyl group, an allyl group, a propargyl group or a benzyl group, R8 is —CHO, —CH2OH, —CH2OR9, wherein R9 is a protecting group, or —CO2H, and X1 is OH, X2 is OH, or X1 and X2 together are O, OS(O)O or OS(O2)O.
A compound having the formula:
- wherein R1 is hydrogen, fluorine, chlorine or SiR5R6R7, wherein R5, R6, and R7 are independently the same or different an alkyl group or an aryl group, R2 is an alkyl group, R3is a protecting group, R4 is an alkyl group, an allyl group, a propargyl group or a benzyl group, R8 is —CHO, —CH2OH, —CH2OR9, wherein R9 is a protecting group, and X1 is OH, X2 is H or OH, or X1 and X2 together are O, OS(O)O or OS(O2)O.
A method of synthesizing a compound having the formula:
- wherein R1 is hydrogen, fluorine, chlorine or SiR5R6R7, wherein R5, R6, and R7 are independently the same or different an alkyl group or an aryl group, R2 is an alkyl group, R3 is a protecting group, R4 is an alkyl group, an allyl group, a propargyl group or a benzyl group, R8 is —CHO, —CH2OH, —CH2OR9, wherein R9 is a protecting group, —CO2H, or —CO2R10, wherein R10 is an alkyl group or an aryl group, and X1 is OH, X2 is H or OH, or X1 and X2 together are O, from a compound having the formula:
- comprising the step of asymmetrically hydroxylating compound (II) or asymmetrically epoxidating compound (II).
A method of synthesizing a compound having the formula:
- wherein R1 is hydrogen, fluorine, chlorine or SiR5R6R7, wherein R5, R6, and R7 are independently the same or different an alkyl group or an aryl group, R2 is an alkyl group, R3 is a protecting group, R4 is an alkyl group, an allyl group, a propargyl group or a benzyl group, R8 is —CHO, —CH2OH, —CH2OR9, wherein R9 is a protecting group —CO2H, or —CO2R10, wherein R10 is an alkyl group or an aryl group, and X1 is OH, X2 is H or OH, or X1 and X2 together are O, OS(O)O or OS(O2)O, comprising the steps of:
- a) converting the ketone of the compound:
- to an alkene to synthesize a compound having the formula:
- b) asymmetrically hydroxylating compound (II) or asymmetrically epoxidating compound (II).
A compound having the formula:
- wherein R1 is SiR5R6R7, wherein R5, R6, and R7 are independently the same or different an alkyl group or an aryl group, R2 is an alkyl group, R3 is a protecting group, R4 is an alkyl group, an allyl group, a propargyl group or a benzyl group, R8 is —CHO, —CH2OH, —CH2OR9, wherein R9is a protecting group, —CO2H, or —CO2R10 wherein R10, is an alkyl group or an aryl group, and X1 is OH, X2 is H or OH, or X1 and X2 together are O, OS(O)O or OS(O2)O.
Dependencies are inferred from the claim text.