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Review | Regular issue | Vol 85, No. 6, 2012, pp.1255-1298
Published online, 14th March, 2012
DOI: 10.3987/REV-12-730
Total Synthesis of Tetrahydropyran-Containing Natural Products Exploiting Intramolecular Oxa-Conjugate Cyclization

Haruhiko Fuwa*

*Graduate School of Life Sciences, Tohoku University, 2-1-1, Katahira, Aoba-ku, Sendai, 980-8577, Japan

Abstract

A growing number of tetrahydropyran-containing biologically active substances are being discovered from nature. Intramolecular oxa-conjugate cyclization (IOCC) is known as one of the most powerful methodologies for the stereoselective synthesis of substituted tetrahydropyran derivatives, although there is clearly room for methodological improvement. In this review, we describe our successful total synthesis of tetrahydropyran-containing natural products by exploiting IOCC and the discoveries that we have made during the course of the synthetic campaigns.