論文雑誌「Chemical Science」のカバーアートを制作しました［中央大学］

Total synthesis and complete configurational assignment of amphirionin-2
Shota Kato, Daichi Mizukami, Tomoya Sugai, Masashi Tsuda and Haruhiko Fuwa

Abstract

Amphirionin-2 is a linear polyketide metabolite that exhibits potent and selective cytotoxic activity against certain human cancer cell lines. We disclose herein the first total synthesis of amphirionin-2 and determination of its absolute configuration. Our synthesis featured an extensive use of cobalt-catalyzed Mukaiyama-type cyclization of γ-hydroxy olefins for stereoselective formation of all the tetrahydrofuran rings found in the natural product, and a late-stage Stille-type coupling for convergent assembly of the entire carbon backbone. Four candidate diastereomers of amphirionin-2 were synthesized in a unified, convergent manner, and their spectroscopic/chromatographic properties were compared with those of the authentic material. The present study culminated in the reassignment of the C5/C7 relative configuration, assignment of the C12/C18 relative configuration, and determination of the absolute configuration of amphirionin-2.

The article was first published on 20 Nov 2020
Chem. Sci., 2021,12, 872-879
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