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Review | Special issue | Vol 95, No. 1, 2017, pp.81-115
Published online, 8th December, 2016
DOI: 10.3987/REV-16-SR(S)2
Strategies for Brevisamide Synthesis, Based on the Method for Constructing the Tetrahydropyranyl Core

Takeo Sakai and Yuji Mori*

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan

Abstract

Brevisamide is a monocyclic ether alkaloid produced by the red tide dinoflagellate Karenia brevis. Brevisamide has attracted the attention of organic chemists because it is the smallest molecule that can be used to understand the biosynthetic 6-endo epoxide cyclization of polycyclic ethers. Within nine years of its discovery, several diverse approaches to synthesizing this monocyclic ether amide have been explored, culminating in the publication of eight total and seven formal total syntheses. In the first part of this review, we discuss strategies for the introduction of the key elements—the (2E,4E)-3,4-dimethyl-2,4-heptadienal side chain, acetamide side chain, C9 axial methyl group, and tetrahydropyran (THP) core. In the following sections, each of the total and formal syntheses is overviewed, based on the method for constructing the THP core.