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Lactone Kinetic Resolution by Acylation – Application to the Enantioselective Synthesis of Estrane Derivatives
Author(s) -
Wilmouth Serge,
Durand AnneCatherine,
Goretta Sarah,
Ravel Christophe,
Moraleda Delphine,
Giorgi Michel,
Pellissier Hélène,
Santelli Maurice
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500380
Subject(s) - chemistry , kinetic resolution , acylation , enantioselective synthesis , alkylation , lactone , organic chemistry , stereochemistry , catalysis
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)