Synthesis 2006(16): 2748-2752  
DOI: 10.1055/s-2006-942500
PAPER
© Georg Thieme Verlag Stuttgart · New York

Thallium(III)-Mediated Ring Contraction of cis-Octalins: An Approach for the Diastereoselective Construction of the nor-Bakkane Skeleton

Helena M. C. Ferraz*, Tiago O. Vieira, , Jr Luiz F. Silva
Instituto de Química, Universidade de São Paulo, CP 26077, CEP 05513-970, São Paulo SP, Brazil
Fax: +55(11)8155579; e-Mail: hmferraz@iq.usp.br;
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Publikationsverlauf

Received 6 April 2006
Publikationsdatum:
19. Juli 2006 (online)

Abstract

A new approach for the diastereoselective synthesis of cis-hydrindanes bearing important structural features of the bakkane skeleton is described. The key step in such a sequence is a thallium trinitrate mediated oxidative rearrangement of cis-octalins. The ring-contraction products thus obtained were elaborated in a diastereoselective fashion into hydrindanes bearing a quaternary center.

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The X-ray data have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 605577.