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Synfacts 2011(5): 0521-0521  
DOI: 10.1055/s-0030-1259823
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Cascade Diels-Alder/Carbocyclization Approach to Hydrindanes

Contributor(s): Mark Lautens, Stephen G. Newman
Y. Han, L. Zhu, Y. Gao, C.-S. Lee*
Peking University Shenzhen Graduate School, P. R. of China
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Publikationsdatum:
15. April 2011 (online)

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Significance

The 6,5-fused bicyclic carbocycle motif (hydrindane) is embedded in the backbone of numerous natural products. The authors present a highly convergent approach to cis-­hydrindanes utilizing a Lewis acid catalyzed intermolecular Diels-Alder, intramolecular carbocyclization cascade. Zinc bromide was found to be the most efficient catalyst, activating the substrate for both steps of the domino sequence, and providing improved diastereoselectivity over similar zinc species.