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Synfacts 2006(12): 1193-1193
DOI: 10.1055/s-2006-955591
DOI: 10.1055/s-2006-955591
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Ciguatoxin (CTX1B)
Contributor(s):Philip KocienskiM. Inoue*, K. Miyazaki, Y. Ishihara, A. Tatami, Y. Ohnuma, Y. Kawada, K. Komano, S. Yamashita, N. Lee, M. Hirama*
Tohoku University, Sendai, Japan
Total Synthesis of Ciguatoxin and 51-HydroxyCTX3C
J. Am. Chem. Soc. 2006, 128: 9352-9354
Tohoku University, Sendai, Japan
Total Synthesis of Ciguatoxin and 51-HydroxyCTX3C
J. Am. Chem. Soc. 2006, 128: 9352-9354
Further Information
Publication History
Publication Date:
22 November 2006 (online)
Key words
radical cyclization - annulation - ring-closing metathesis
Significance
This awesome synthesis of ciguatoxin features the use of a thioether group to (a) promote linkage of fragments A and B via the formation of an O,S-acetal C and (b) serve as a radical precursor in the cyclization of D to E.
Comment
The 7-exo-trig cyclization (D to E) of the C30 radical onto the acrylate moiety at C29 was favored over the 6-exo-trig cyclization onto C26 by using the pentafluorophenyl ester.