Tetrahedron

Asymmetric total synthesis of enantiopure (−)-methyl jasmonate via catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfone

H Takeda, H Watanabe, M Nakada

Index: Takeda, Hiroyuki; Watanabe, Hideaki; Nakada, Masahisa Tetrahedron, 2006 , vol. 62, # 34 p. 8054 - 8063

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Citation Number: 33

Abstract

A new asymmetric total synthesis of enantiopure (−)-methyl jasmonate is described. This synthesis was accomplished starting from the new enantiopure building block prepared via the catalytic asymmetric intramolecular cyclopropanation (IMCP) of the α-diazo-β-keto 1- naphthyl sulfone, which was devised to give good selectivity both in the IMCP reaction and in the C-alkynylation of the intermediate required for the total synthesis of enantiopure (−)- ...