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Total synthesis and complete configurational assignment of amphirionin-2

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.

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Article information


Submitted
02 Nov 2020
Accepted
19 Nov 2020
First published
20 Nov 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021, Accepted Manuscript
Article type
Edge Article

Total synthesis and complete configurational assignment of amphirionin-2

S. Kato, D. Mizukami, T. Sugai, M. Tsuda and H. Fuwa, Chem. Sci., 2021, Accepted Manuscript , DOI: 10.1039/D0SC06021F

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