Synthesis of the common FGHI-ring part of ciguatoxins |
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Authors: | Ayumi Takizawa Eriko Doi Akio Murai Hidetoshi Kawai Takanori Suzuki |
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Institution: | Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan |
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Abstract: | The common FGHI-ring part (2) of ciguatoxins has been synthesized from the F- and I-ring parts (6 and 5, respectively). The Nozaki-Hiyama-Kishi coupling of 6 with 5 followed by regio- and stereoselective epoxidation at C29 and C30 afforded an epoxide (4), which was transformed into a tricyclic compound (3) corresponding to the F-HI-ring part by 6-exo-epoxide opening and the subsequent inversion of the C29 stereocenter. Reductive cyclization of 3 forming the C31-O26 bond of the G-ring successfully produced 2. |
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Keywords: | Ciguatoxin Natural product synthesis trans-Fused polycyclic ether Convergent synthesis |
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