Journal
TETRAHEDRON
Volume 64, Issue 29, Pages 6884-6900Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.02.066
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Funding
- NIGMS NIH HHS [R01 GM031077-24, R01 GM031077, R01 GM031077-21, R01 GM031077-22, R01 GM031077-20, R01 GM025439, R01 GM025439-23, R01 GM025439-22, R01 GM025439-24A2, R01 GM031077-23] Funding Source: Medline
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The first application of the Pauson-Khand reaction (PKR) to the synthesis of azabridged bicyclic structures is described. Compounds containing azabicyclo[3.3.1]nonane and azabicyclo[3.2.1]octane rings fused to cyclopentenones were efficiently constructed via the PKR of cis-2,6-disubstituted N-acyl piperidine enyne substrates, many of which can be readily prepared from 4-methoxypyridine in a few steps. Moreover, the PKR of cis-2,6-substituted piperazine enynes allowed the preparation of diazabicyclo[3.3.1]nonanes fused to cyclopentenones. This new strategy for the synthesis of azabridged bicyclic frameworks was exploited as a key step in a concise, enantioselective total synthesis of the macroline alkaloid (-)-alstonerine. (C) 2008 Elsevier Ltd. All rights reserved.
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