Convenient Route to Both Enantiomerically Pure Forms of trans-4,5-Dihydroxy-2-cyclopenten-1-one: Efficient Synthesis of the Neocarzinostatin Chromophore Core
- 1 June 2001
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 74 (6) , 997-1008
- https://doi.org/10.1246/bcsj.74.997
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.Keywords
This publication has 37 references indexed in Scilit:
- Synthetic Study of Kedarcidin Chromophore: Revised StructureJournal of the American Chemical Society, 1997
- Synthesis of a Nine‐Membered Cyclic Analogue of the Neocarzinostatin Chromophore and Its DNA‐Cleaving ActivityAngewandte Chemie International Edition in English, 1993
- Chemistry and structure elucidation of the kedarcidin chromophoreJournal of the American Chemical Society, 1993
- Evidence for aminoglycoside participation in thiol activation of neocarzinostatin chromophore. Synthesis and reactivity of the epoxy dienediyne coreJournal of the American Chemical Society, 1992
- Synthesis and DNA cleaving abilities of functional neocarzinostatin chromophore analogs. Base discrimination by a simple alcoholJournal of the American Chemical Society, 1991
- Enantioselective synthesis of the epoxy diyne core of neocarzinostatin chromophoreJournal of the American Chemical Society, 1991
- A total synthesis of racemic and optically active terrein (trans-4,5-dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one).Tetrahedron: Asymmetry, 1990
- Stereochemical assignment of neocarzinostatin chromophore. Structures of neocarzinostatin chromophore-methyl thioglycolate adductsJournal of the American Chemical Society, 1988
- Studies on DNA - active agents: The synthesis of the parent carbocyclic subunit of neocarzinostatin chromophore ATetrahedron Letters, 1988
- The structure of neocarzinostatin chromophore possessing a novel bicyclo-[7,3,0]dodecadiyne systemTetrahedron Letters, 1985