2015 · ORGANIC LETTERS

Synthetic Studies toward the C32-C46 Segment of Hemicalide. Assignment of the Relative Configuration of the C36-C42 Subunit

Specklin, Simon, Boissonnat, Guillaume, Lecourt, Camille, Sorin, Geoffroy, Lannou, Marie-Isabelle, Ardisson, Janick, Sautel, Francois, Massiot, Georges, Meyer, Christophe, Cossy, Janine

Journal: ORGANIC LETTERS
Année: 2015
Volume: 17
Numéro: 10
Pages: 2446-2449
Mois: MAY 15
DOI: 10.1021/acs.orglett.5b00955

Abstract

The synthesis of five diastereomeric model compounds incorporating the C32-C46 segment of the antitumor marine natural product hemicalide has been achieved through a convergent approach relying on the 1,4-addition of an alkenyl boronate to an alpha,beta-unsaturated delta-lactone followed by alpha- hydroxylation of an enolate and a Julia-Kocienski olefination. Comparison of the H-1 and C-13 NMR data of the model compounds with those of hemicalide enabled the assignment of the relative configuration of the C36-C42 subunit.

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