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Communication | Special issue | Vol 99, No. 1, 2019, pp.111-117
Published online, 31st October, 2018
DOI: 10.3987/COM-18-S(F)40
Total Synthesis of (–)-Zephyranthine

Koki Ishii, Yuna Seki-Yoritate, Mizuki Ishibashi, Ming Wai Liaw, Takeshi Oishi, Takaaki Sato,* and Noritaka Chida*

*Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku Yokohama 223-8522, Japan

Abstract

Stereoselective total synthesis of (–)-zephyranthine 1 based on the chiral pool approach starting from D-arabinose is described. The three consecutive chiral centers in (–)-zephyranthine were effectively constructed by the sequential [3,3] sigmatropic rearrangements (Claisen, Overman, and Claisen rearrangements) with chirality transfer of the hydroxy groups in D-arabinose.