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Synthetic Studies on Ciguatoxin: A Convergent Strategy for Construction of the F-M Ring Framework
Masayuki Inoue1, Makoto Sasaki1, Kazuo Tachibana1
1Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5800-6898, ktachi@chem.s.u-tokyo.ac.jp.
Abstract:
Exceptional neurotoxicity is associated with ciguatoxin. The ciguatoxin mimic 1, which contains the F-M framework of the natural product, has been prepared through a convergent synthesis. The two key steps were a Lewis acid mediated intramolecular reaction of a γ-alkoxyallylsilane with an acetal group and an SmI2 -mediated intramolecular Reformatsky reaction that permitted construction of the annelated hexahydrooxonin ring system.
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