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

K. Toyama, S. Iguchi, H. Sakazaki, T. Oishi, M. Hirama

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)997-1008
Number of pages12
JournalBulletin of the Chemical Society of Japan
Volume74
Issue number6
DOIs
Publication statusPublished - Jun 1 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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