Method for producing asymmetric conjugated diyne compound and method for producing Z,Z-conjugated diene compound using the same

A method for producing an asymmetric conjugated diyne compound, comprising:

• a step of subjecting a terminal alkyne compound of formula (1):
• HC≡C—Z1—Y1 (1)
• wherein Y1 is a hydrogen atom;
• a halogen atom;
• a hydroxyl group;
• a hydroxyl group protected with a protecting group that forms an ester, ether or acetal;
• or a formyl group protected with a protecting group that forms thioacetal or acetal;
• and Z1 is a linear, branched, cyclic or polycyclic divalent C1-14 hydrocarbon group having an optional double bond or triple bond;
• to a coupling reaction with an alkynyl halide of formula (2):
• Y2—Z2—C≡C—X (2)
• wherein Y2 is a hydrogen atom;
• a halogen atom;
• a hydroxyl group;
• a hydroxyl group protected with a protecting group that forms an ester, ether or acetal;
• or a formyl group protected with a protecting group that forms thioacetal or acetal;
• Z2 is a linear, branched, cyclic or polycyclic divalent C1-14 hydrocarbon group having an optional double bond or triple bond;
• X is a halogen atom;
• and the Y2—Z2 is not the same as the Y1—Z1;
• by using sodium borohydride in water and an organic solvent in the presence of a copper salt and a base to obtain the asymmetric conjugated diyne compound of formula (3):
• Y2—Z2—C≡C—C≡C—Z1—Y1 (3).