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Communication | Special issue | Vol 80, No. 2, 2010, pp.811-818
Published online, 18th September, 2009
DOI: 10.3987/COM-09-S(S)89
Synthesis of the 1,2-Anti Type of 3E-Alkene-1,2,5-triol Derivatives

Yuichi Kobayashi,* Akira Takeuchi, and Hatsuhiko Hattori

*Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan

Abstract

We invented an efficient method to obtain 3E-alkene-1,2,5-triol derivatives with 1,2-anti stereochemistry from the 2Z,4E-alkadienyl alcohol derivatives, which were synthesized by using nickel-catalyzed coupling between lithium 1E-alkenyl borates and 1-halo-1Z-alken-3-ols. The method involves (1) asymmetric dihydroxylation at the E olefin moiety of the dienyl alcohol derivatives followed by formation of a cyclic carbonates; (2) palladium-catalyzed reaction with AcOH in the presence of Et3N. The method was applied successfully to the synthesis of the C6–C20 part of trioxilin A3.