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

Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India. pk.tripathi@ncl.res.in

Organic & biomolecular chemistry 2012 Sep 14

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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.

Citation

Pradeep Kumar, Abhishek Dubey, Anand Harbindu. Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and L-(-)-CCG-II. Organic & biomolecular chemistry. 2012 Sep 14;10(34):6987-94