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Synthesis 2006(16): 2748-2752
DOI: 10.1055/s-2006-942500
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
Further Information
Received
6 April 2006
Publication Date:
19 July 2006 (online)
Publication History
Publication Date:
19 July 2006 (online)
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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.
Keywords
bakkanes - ring contraction - thallium(III) - hydrindanes - oxidative rearrangement
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References
The X-ray data have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 605577.