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Paper | Special issue | Vol 74, No. 1, 2007, pp.617-627
Published online, 16th October, 2007
DOI: 10.3987/COM-07-S(W)39
Formal Total Synthesis of Hemibrevetoxin B via the Intramolecular Allylation Followed by Ring-Closing Metathesis

Isao Kadota,* Takashi Abe, Yukako Ishitsuka, Abeda S. Touchy, Ryoko Nagata, and Yoshinori Yamamoto

*Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan


A formal total synthesis of hemibrevetoxin B (1) is described. Intramolecular allylation of α-chloroacetoxy ether 10, prepared from carboxylic acid 11 and alcohol 12, was carried out with MgBr2·OEt2 to give 27. Ring-closing metathesis of 27 furnished tetracycle 29, which was converted to a known synthetic intermediate 9, to complete a formal total synthesis of 1.