Multiple chirality transfers in the enantioselective synthesis of 11-O-debenzoyltashironin. Chiroptical analysis of the key cascade

Alessandra Polara; Silas P Cook; Samuel J Danishefsky

doi:10.1016/j.tetlet.2008.07.139

Multiple chirality transfers in the enantioselective synthesis of 11-O-debenzoyltashironin. Chiroptical analysis of the key cascade

Tetrahedron Lett. 2008 Oct 6;49(41):5906-5908. doi: 10.1016/j.tetlet.2008.07.139.

Authors

Alessandra Polara¹, Silas P Cook, Samuel J Danishefsky

Affiliation

¹ Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA.

Abstract

The mechanism of the cascade oxidative dearomatization-transannular Diels Alder was investigated in the context of an asymmetric route to (-)-11-O-debenzoyltashironin. Although the oxidative dearomatization provides two acetal intermediates, the transannular Diels-Alder proceeds spontaneously from only one of the acetal isomers. Access to enantioenriched tetracyclic adduct was gained through the use of optically active allene.

Abstract

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