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

TitleEnantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and L-(-)-CCG-II
Publication TypeJournal Article
Year of Publication2012
AuthorsKumar, P, Dubey, A, Harbindu, A
JournalOrganic & Biomolecular Chemistry
Volume10
Issue34
Pagination6987-6994
Date PublishedJUL
Type of ArticleArticle
ISSN1477-0520
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.

DOI10.1039/c2ob25622c
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.568
Divison category: 
Organic Chemistry