Catalytic asymmetric access to alpha,beta unsaturated delta-lactones through a vinylogous aldol reaction: Application to the total synthesis of the Prelog-Djerassi lactone

Authors
Bluet, G Bazan-Tejeda, B Campagne, JM
Citation
G. Bluet et al., Catalytic asymmetric access to alpha,beta unsaturated delta-lactones through a vinylogous aldol reaction: Application to the total synthesis of the Prelog-Djerassi lactone, ORG LETT, 3(23), 2001, pp. 3807-3810
Citations number
41
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
23
Year of publication
2001
Pages
3807 - 3810
Database
ISI
SICI code
1523-7060(20011115)3:23<3807:CAATAU>2.0.ZU;2-Z
Abstract
[GRAPHICS] A one-step catalytic asymmetric access to alpha,beta unsaturated delta -lac tones is described, using a vinylogous Mukaiyama-aidol reaction between a g amma -substituted dienolate and various aldehydes in the presence of Carrei ra catalyst CuF-(S)-tolBinap. This methodology has been further applied to a straightforward access to the Prelog-Djerassi lactone.