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Review | Regular issue | Vol 85, No. 3, 2012, pp.587-613
Published online, 7th February, 2012
DOI: 10.3987/REV-12-727
Total Synthesis of Aspergillides A, B, and C

Tomohiro Nagasawa and Shigefumi Kuwahara*

*Graduate School of Agricultural Science, Tohoku University, 1-1, Tsutsumidori, Amamiya, Aoba-ku, Sendai, 981-8555, Japan

Abstract

Aspergillides A, B, and C are cytotoxic macrolides produced by the marine-derived fungus Aspergillus ostianus strain TUF 01F313. The unique molecular architectures of the aspergillides featuring 14-membered marocyclic structures embedded with a tetrahydro- or dihydropyran unit have attracted significant attention from the synthetic chemistry community, and thereby various synthetic approaches to these structurally as well as pharmacologically intriguing molecules have been reported by as many as 12 research groups in the past 3 years. This review describes all of the syntheses disclosed to date, focusing mainly on the methodologies employed for the diastereoselective installation of the pyran ring systems.