Lactone Kinetic Resolution by Acylation - Application to the Enantioselective Synthesis of Estrane Derivatives

The acylation of an excess of racemic spirolactone 1 (6,9‐divinyl‐1‐oxaspiro[4.4]nonan‐2‐one) enolate by protected methyl (S)‐lactate or (–)‐bornyl carbonate occurs with a kinetic resolution. The resulting lactones were alkylated with 1‐iodobenzocyclobutenes to afford compounds that serve as precurs...

Full description

Saved in:
Bibliographic Details
Published in:European Journal of Organic Chemistry 2005-11, Vol.2005 (22), p.4806-4814
Main Authors: Wilmouth, Serge, Durand, Anne-Catherine, Goretta, Sarah, Ravel, Christophe, Moraleda, Delphine, Giorgi, Michel, Pellissier, Hélène, Santelli, Maurice
Format: Article
Language:English
Subjects:
Acylation
Asymmetric synthesis
Chiral pool
Kinetic resolution
Steroids
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The acylation of an excess of racemic spirolactone 1 (6,9‐divinyl‐1‐oxaspiro[4.4]nonan‐2‐one) enolate by protected methyl (S)‐lactate or (–)‐bornyl carbonate occurs with a kinetic resolution. The resulting lactones were alkylated with 1‐iodobenzocyclobutenes to afford compounds that serve as precursors to nonracemic steroids such as 11α‐alkyloxycarbonyl‐11β,13β‐(γ‐carbolactone)‐17β‐vinylgonatri‐1,3,5(10)‐enes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200500380