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Total Synthesis of Brevetoxin-B

2004; American Chemical Society; Volume: 126; Issue: 44 Linguagem: Inglês

10.1021/ja0449269

1943-2984

Goh Matsuo, Koji Kawamura, Nobuyuki Hori, Hiroko Matsukura, Tadashi Nakata,

Oxidative Organic Chemistry Reactions

Brevetoxin-B (BTX-B), produced by the red tide organism, Gymnodium breve Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. The structural feature is a trans-fused polycyclic ether ring system with 23 stereocenters. Its unique, complex structure and potent biological activity have attracted the attention of synthetic organic chemists. Total synthesis of BTX-B has been accomplished via the coupling of the ABCDEFG and IJK-ring segments, each ether ring of which was stereoselectively and efficiently constructed on the basis of SmI2-induced intramolecular cyclization, 6-endo-cyclization of hydroxy epoxide, ring-closing olefin metathesis, and SmI2-induced intramolecular Reformatsky-type reaction. Several kinds of double reactions at the left and right sides were efficiently used through the synthesis.