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Paper | Regular issue | Vol 89, No. 1, 2014, pp.127-142
Published online, 3rd December, 2013
DOI: 10.3987/COM-13-12880
■ Synthesis and Cyclization of a Proposed Biosynthetic Epoxy Intermediate of a Marine Monocyclic Ether Amide, Brevisamide

Tomohiro Shirai, Yuki Takimoto, Takefumi Kuranaga, Kazuo Tachibana, Masayuki Satake,* Daniel G. Baden, and Jeffrey L. C. Wright

*Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract

Proposed biosynthetic intermediates of a marine monocyclic ether alkaloid, brevisamide (1) were synthesized for biosynthetic studies on the marine ladder-frame polyethers. The intermediates comprising a linear backbone with trans-olefin (2) and epoxide (3) functionality were synthesized via a Suzuki–Miyaura cross coupling reaction and a Katsuki–Sharpless asymmetric epoxidation reaction. In protic solvents, 3 was unstable and readily cyclized to an unnatural 5-membered ether ring compound (4).