Issue 34, 2012
From the journal:

Organic & Biomolecular Chemistry

Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II†

Pradeep Kumar,*a   Abhishek Dubeya  and  Anand Harbindua  

* Corresponding authors

a Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India
E-mail: pk.tripathi@ncl.res.in
Fax: +91-20-25902629
Tel: +91-20-25902050

Abstract

An efficient high yielding improved method for the enantio- and diastereoselective cyclopropanation of chiral epoxides using triethylphosphonoacetate and base (Wadsworth–Emmons cyclopropanation) is reported. The utility of this protocol is illustrated by concise and practical synthesis of cascarillic acid, grenadamide and L-(−)-CCG-II, a cyclopropane containing natural products.

Graphical abstract: Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II

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Article information

DOI
https://doi.org/10.1039/C2OB25622C
Article type
Paper
Submitted
26 Mar 2012
Accepted
03 Jul 2012
First published
04 Jul 2012

Org. Biomol. Chem., 2012,10, 6987-6994

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Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and L-(−)-CCG-II

P. Kumar, A. Dubey and A. Harbindu, Org. Biomol. Chem., 2012, 10, 6987 DOI: 10.1039/C2OB25622C

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