Total Synthesis of Putative Chagosensine.

Angewandte Chemie
Marc HeinrichAlois Fürstner

Abstract

The marine macrolide chagosensine is the only natural product known to date that embodies a Z,Z-configured chloro-1,3-diene unit. This distinguishing substructure was prepared by a sequence of palladium-catalyzed 1,2-distannation of an alkyne precursor, regioselective Stille cross-coupling at the terminus of the resulting bisstannyl alkene with an elaborated alkenyl iodide, followed by chloro-destannation of the remaining internal site. The preparation of the required substrates centered on cobalt-catalyzed oxidative cyclization reactions of hydroxylated olefin precursors, which allowed the 2,5-trans-disubstituted tetrahydrofuran rings, embedded into each building block, to be formed with excellent selectivity. The highly strained macrolactone could ultimately be closed under forcing Yamaguchi conditions. Comparison of the spectral data of the synthetic sample with those of authentic chagosensine methyl ester confirmed that the structure of this intriguing compound has been mis-assigned by the isolation team.

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Citations

Nov 7, 2018·Chemistry : a European Journal·Bernhard WölflAlois Fürstner
Jun 13, 2019·Chemistry : a European Journal·Lauren E Longobardi, Alois Fürstner
Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Sep 19, 2020·Angewandte Chemie·Saskia SchulthoffAlois Fürstner
Jun 25, 2021·Chemical Science·Shota KatoHaruhiko Fuwa
Mar 7, 2020·Journal of the American Chemical Society·Marc HeinrichAlois Fürstner

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