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Paper | Special issue | Vol 88, No. 2, 2014, pp.1175-1189
Published online, 18th September, 2013
DOI: 10.3987/COM-13-S(S)79
■ Total Synthesis of the Proposed Structures of Eushearilide

Takayasu Yamauchi,* Jun-ichi Takidaira, Kenya Okamoto, Takaya Sugiura, Hiroki Horikoshi, Shintaro Kudo, Shigeru Sasaki, Noriko Mizushima, and Kimio Higashiyama

*Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Total synthesis of (3R,16Z,20E,23S)- and (3R,16Z,20E,23R)-eushearilide was accomplished in 15 steps, respectively. Using either enantiomer of one of the four building blocks to assemble the phosphonium salt for the latter Wittig reaction, two diastereomers of eushearilide were prepared. Shiina macrolactonization (2-methyl-6-nitrobenzoic anhydride) was a key step in production of the 24-membered lactone in high yield.