Total syntheses of the phytotoxic lactones herbarumin I and II and a synthesis-based solution of the pinolidoxin puzzle

…, R Goddard, CW Lehmann, R Mynott

Index: Fuerstner, Alois; Radkowski, Karin; Wirtz, Conny; Goddard, Richard; Lehmann, Christian W.; Mynott, Richard Journal of the American Chemical Society, 2002 , vol. 124, # 24 p. 7061 - 7069

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Citation Number: 196

Abstract

A concise approach to a family of potent herbicidal 10-membered lactones is described on the basis of ring-closing metathesis (RCM) as the key step for the formation of the medium- sized ring. This includes the first total syntheses of herbarumin I (1) and II (2) as well as the synthesis of several possible macrolides of the pinolidoxin series. A comparison of their spectral and analytical data with those of the natural product allowed us to establish the ...