Synthesis and Refunctionalization of Hexahydro-naphthalenone Systems

Abstract

Cis- and trans-hexahydronaphthalenones 8 and 9 were readily obtained by Diels-Alder addition and epimerization. Highly stereoselective reduction of 9 furnished the alcohol 10, which could be converted to the epimeric alcohol 11 by Mitsunobu inversion. The propionate 13 derived from 11 failed to undergo a Claisen re­arrangement.

Key words

cycloaddition - Diels-Alder - Claisen rearrangement

References

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Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as private communication no. CCDC 231006 (Klaus Harms, University of Marburg, 2004). These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing [e-mail], or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: [phone].