143397-35-7Relevant academic research and scientific papers
Total Synthesis of (+)-Latrunculin A, an Ichthyotoxic Metabolite of the Sponge Latrunculia magnifica, and Its C-15 Epimer
White, James D.,Kawasaki, Motoji
, p. 5292 - 5300 (2007/10/02)
Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica 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, β-keto ester 27, and phosphonium salt 26, which established the conjugated E,Z-diene moiety of 31.The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection.Final lactonization of 47 was carried out using the Mitsunobu protocol.A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.
