Lactone Kinetic Resolution by Acylation – Application to the Enantioselective Synthesis of Estrane Derivatives | Zendy

Wilmouth Serge | Zendy; Durand AnneCatherine | Zendy; Goretta Sarah | Zendy; Ravel Christophe | Zendy; Moraleda Delphine | Zendy; Giorgi Michel | Zendy; Pellissier Hélène | Zendy; Santelli Maurice | Zendy

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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)

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