title: Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and L-(-)-CCG-II.
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.
authors: Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India. pk.tripathi@ncl.res.in
authors: Pradeep
authors: P
authors: Kumar
authors: Abhishek
authors: A
authors: Dubey
authors: Anand
authors: A
authors: Harbindu
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000600:Amino Acids, Dicarboxylic / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000577:Amides; D000600:Amino Acids, Dicarboxylic; D003521:Cyclopropanes; D004852:Epoxy Compounds; D005227:Fatty Acids; C112731:grenadamide; C015766:cyclopropanecarboxylic acid; C035261:(alpha-carboxycyclopropyl)glycine