A novel, efficient, diastereo- and enantioselective Mukaiyama aldol-based synthesis of a vinyl cyclopentanone core derivative of viridenomycin

Andrei S Batsanov; Jonathan P Knowles; Andrew P Lightfoot; Graham Maw; Carl E Thirsk; Steven J R Twiddle; Andrew Whiting

doi:10.1021/ol7025262

A novel, efficient, diastereo- and enantioselective Mukaiyama aldol-based synthesis of a vinyl cyclopentanone core derivative of viridenomycin

Org Lett. 2007 Dec 20;9(26):5565-8. doi: 10.1021/ol7025262. Epub 2007 Nov 17.

Authors

Andrei S Batsanov¹, Jonathan P Knowles, Andrew P Lightfoot, Graham Maw, Carl E Thirsk, Steven J R Twiddle, Andrew Whiting

Affiliation

¹ Department of Chemistry, Durham University, Science Laboratories, South Road, Durham DH1 3LE, UK.

PMID: 18020354
DOI: 10.1021/ol7025262

Abstract

A strategy has been developed for a rapid seven-step construction of a chiral, nonracemic vinyl cyclopentanone building block as part of a synthetic approach to viridenomycin, using a diastereo- and enantioselective Mukaiyama aldol and intramolecular Knoevenagel condensation as key steps.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Cyclopentanes / chemistry*
Lactams / chemical synthesis
Stereoisomerism

Substances

Aldehydes
Cyclopentanes
Lactams
cyclopentanone
viridinomycin
3-hydroxybutanal