Intramolecular vinyl quinone Diels-Alder reactions: asymmetric entry to the cordiachrome core and synthesis of (-)-isoglaziovianol.

Org Lett

Department of Chemistry and Center of Integrated Protein Science, University of Munich, Butenandtstrasse 5-13 (F4.086), 81377 Munich, Germany.

Published: September 2013

A short and asymmetric entry to the core structure of the cordiachromes has been developed, allowing access to (-)-isoglaziovianol in seven steps. Our synthesis includes a Trost asymmetric allylic alkylation and a reaction cascade triggered by a vinyl quinone Diels-Alder reaction and followed by intramolecular nucleophilic interception.

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http://dx.doi.org/10.1021/ol401787nDOI Listing

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