Organic & Biomolecular Chemistry 2012-09-14

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, Abhishek Dubey, Anand Harbindu

Index: Org. Biomol. Chem. 10(34) , 6987-94, (2012)

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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.