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. 2017 Jan 4;15(2):408-415.
doi: 10.1039/c6ob02587k.

Universal access to megastigmanes through controlled cyclisation towards highly substituted cyclohexenes

Affiliations

Universal access to megastigmanes through controlled cyclisation towards highly substituted cyclohexenes

José A González-Delgado et al. Org Biomol Chem. .

Abstract

We report the selective formation of cyclohexenes with a tetrasubstituted double bond, the structural key element of megastigmanes. For this purpose the ZrCl4-mediated epoxide ring opening of epoxy-geranylacetone was employed. This approach provides a universal entry to the preparation of the members of the megastigmane family, which was exemplified in the asymmetric synthesis of tectoionol B.

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