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Communication | Special issue | Vol 79, No. 1, 2009, pp.325-330
Published online, 11th September, 2008
DOI: 10.3987/COM-08-S(D)7
Design and Synthesis of a Conformationally Restricted Analogue of the EFGH-ring System of Ciguatoxin

Nayoung Lee, Masayuki Inoue,* and Masahiro Hirama*

*1Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan

Abstract

The fused-hexahydrooxonine (F-ring) of ciguatoxin (CTX), as well as its EFGH-ring fragment, undergoes a slow conformational change between two conformers in solution. In this paper, we designed and synthesized a conformationally restricted analogue of the EFGH-ring system of ciguatoxin. Chemo- and stereoselective epoxidation of the F-ring successfully impeded the dynamic behavior without affecting the overall three-dimensional shape of the molecule.