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Mar. Drugs 2016, 14(4), 65; doi:10.3390/md14040065

Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product

Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan
Academic Editor: Orazio Taglialatela-Scafati
Received: 25 January 2016 / Revised: 15 March 2016 / Accepted: 17 March 2016 / Published: 25 March 2016

Abstract

Tetrahydropyrans are structural motifs that are abundantly present in a range of biologically important marine natural products. As such, significant efforts have been paid to the development of efficient and versatile methods for the synthesis of tetrahydropyran derivatives. Neopeltolide, a potent antiproliferative marine natural product, has been an attractive target compound for synthetic chemists because of its complex structure comprised of a 14-membered macrolactone embedded with a tetrahydropyran ring, and twenty total and formal syntheses of this natural product have been reported so far. This review summarizes the total and formal syntheses of neopeltolide and its analogues, highlighting the synthetic strategies exploited for constructing the tetrahydropyran ring. View Full-Text
Keywords: synthetic methods; tetrahydropyrans; oxocarbenium ions; hetero-Diels-Alder cycloadditions; oxa-Michael reactions; palladium-catalyzed alkoxycarbonylations; oxymercurations; radical cyclizations; ring-closing metathesis synthetic methods; tetrahydropyrans; oxocarbenium ions; hetero-Diels-Alder cycloadditions; oxa-Michael reactions; palladium-catalyzed alkoxycarbonylations; oxymercurations; radical cyclizations; ring-closing metathesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Fuwa, H. Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product. Mar. Drugs 2016, 14, 65.

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