Asymmetric total syntheses of (+)-coronafacic acid and (+)-coronatine, phytotoxins isolated from Pseudomonas syringae pathovars

S Nara, H Toshima, A Ichihara

Index: Nara, Shinji; Toshima, Hiroaki; Ichihara, Akitami Tetrahedron, 1997 , vol. 53, # 28 p. 9509 - 9524

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Citation Number: 32

Abstract

Asymmetric total synthesis of (+)-coronafacic acid (2), was accomplished via intramolecular 1, 6-conjugate addition as the key step. The chiral ester (+)-7 was prepared via two approaches: starting from (R)-(+)-4-acetoxy-2-cyclopenten-1-one (12), and using catalytic asymmetric Michael reactions promoted by heterobimetallic BINOL complexes. Coupling between (+)-2 and the protected coronamic acid 8 and subsequent deprotection by ...