Synlett 2010(2): 207-210  
DOI: 10.1055/s-0029-1218561
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A New Access to the 6,8-Dioxabicyclo[3.2.1]octane Ring System Using a Three-Component Reaction: Enantioselective Synthesis of (+)-iso-exo-Brevicomin

Asmae Bouzianea, Thomas Régniera, François Carreaux*a, Bertrand Carbonia, Christian Bruneaua, Jean-Luc Renaudb
a Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France
e-Mail: francois.carreaux@univ-rennes1.fr;
b Laboratoire Chimie Moléculaire et Thioorganique, UMR CNRS 6507, 6 Bd du Maréchal Juin, 14050 Caen, France
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Received 9 October 2009
Publikationsdatum:
10. Dezember 2009 (online)

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Abstract

The combination of a catalytic hetero-Diels-Alder-­allylboration sequence and a ruthenium-catalyzed isomerization of an allylic alcohol moiety as key steps open a new route for the asymmetric synthesis of 6,8-dioxabicyclo[3.2.1]octane subunits. The application of this strategy to the synthesis of (+)-iso-exo-brevi­comin is also reported.

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