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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Akio Murai合作论文数2Kenshu Fujiwara合作论文数ivision of Chemistry, Graduate School of Science, Hokkaido University2Yuko Ohtaniuchi合作论文数1
Takanori Suzuki合作论文数Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan1
Hidetoshi Kawai合作论文数1Shin-Ichiro Souma合作论文数1Ken Shimawaki合作论文数1Atsushi Takemura合作论文数1
Yasuhito Koyama合作论文数Department of Organic and Polymeric Materials, Tokyo Institute of Technology1Ayumi Takizawa合作论文数1
