Convenient route to both enantiomerically pure forms of trans-4,5-dihydroxy-2-cyclopenten-1-one: Efficient synthesis of the neocarzinostatin chromophore core

Article abstract of DOI:10.1246/bcsj.74.997

An enantioselective synthesis of an epoxybicyclo[7.3.0]dodecenediyne core system of the neocarzinostatin chromophore has been achieved via intramolecular acetylide addition and palladium-mediated coupling of iodocyclopentene 5 with alkyne 6. The key cyclopentene moiety, trans-4,5-dihydroxy-2-cyclopenten-1-one 7, was conveniently prepared in both enantiomerically pure forms via enzymatic desymmetrization of meso-3,4,5-trans,trans-trihydroxycyclopentene derivatives.