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Article Dans Une Revue Journal of Organic Chemistry Année : 2012

Study of the total synthesis of (-)-exiguolide.

Résumé

In this article, we disclose the various routes and strategies we had to explore before finally achieving the total synthesis of (-)-exiguolide ((-)-1). Two first types of approaches were set, both relying on the Trost's domino ene-yne coupling/oxa-Michael reaction that we choose for its ability to control the geometry of the methylacrylate-bearing tetrahydropyrane ring B. In our first approach, we expected to assemble the two main fragments (C14-C21 and C1-C13) by creating the C13-C14 bond through a palladium(0)-catalyzed cross-coupling, but this step failed, unfortunately. In the second approach, which was more linear, we created the C16-C17 bond through condensation of a lithium acetylide on a Weinreb amide, and we assembled the C1-C5 and C6-C21 subunits through Trost's domino ene-yne coupling/oxa-Michael reaction. These two approaches served us to design an ameliorated third strategy, which finally led to the total synthesis of (-)-exiguolide.

Domaines

Chimie organique
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Dates et versions

hal-00741332 , version 1 (12-10-2012)

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Citer

Cyril Cook, Frédéric Liron, Xavier Guinchard, Emmanuel Roulland. Study of the total synthesis of (-)-exiguolide.. Journal of Organic Chemistry, 2012, 77 (16), pp.6728-42. ⟨10.1021/jo301066p⟩. ⟨hal-00741332⟩
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