Function-Oriented Synthesis toward Peloruside A Analogues

Abstract : A convergent and rapid synthesis of original C2,C3-unsaturated, C11,C13-keto-enol macrocycles with a peloruside A skeleton has been developed. These original unsaturated macrocycles constitute valuable platforms to access peloruside A analogues with high diversity. The four-fragment strategy implemented features two aldol-type couplings with the central C12-C14 building block TES-diazoacetone and a late-stage ring-closing metathesis. Enantiopure analogue 18ab showed antiproliferative activity in the low micromolar range on NCI and MCF7 tumor cell lines.
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Submitted on : Tuesday, April 2, 2019 - 1:16:55 PM
Last modification on : Tuesday, July 23, 2019 - 10:36:03 AM

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Anne-Caroline Chany, Frédéric Legros, Heloua Haroun, Uday Kumar Kundu, Bohdan Biletskyi, et al.. Function-Oriented Synthesis toward Peloruside A Analogues. Organic Letters, ACS, 2019, ⟨10.1021/acs.orglett.9b00413⟩. ⟨hal-02087811⟩

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