55795-17-0Relevant academic research and scientific papers
Synthesis of 1,3-dienes of (E,Z) configuration by a three-component coupling strategy
White, James D.,Jensen, Mark S.
, p. 5743 - 5756 (1995)
Three-component coupling of an anionic nucleophile, butadienyltriphenylphosphonium bromide, and an aldehyde gave conjugated dienes of predominantly (E,Z) configuration. Dianions of β-dicarbonyl systems and dicarboxylic acids, and monoanions of sulfones we
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.
