The Journal of Organic Chemistry

Total synthesis of (+)-latrunculin A, an ichthyotoxic metabolite of the sponge Latrunculia magnifica and its C-15 epimer

JD White, M Kawasaki

Index: White, James D.; Kawasaki, Motoji Journal of Organic Chemistry, 1992 , vol. 57, # 20 p. 5292 - 5300

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Citation Number: 76

Abstract

Latrunculin A (l), an icthyotoxic metabolite of the sponge Latrunculia mugnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach. Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24,@- keto ester 27, and phosphonium salt 26, which established the conjugated E, Z-diene ...