The Pauson-Khand Reaction as a New Entry to the Synthesis of Bridged Bicyclic Heterocycles: Application to the Enantioselective Total Synthesis of (-)-Alstonerine.

Tetrahedron
Kenneth A MillerStephen F Martin

Abstract

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-disubstituted 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 alklaoid (-)-alstonerine.

References

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Apr 10, 2003·Journal of the American Chemical Society·Alexander DeitersStephen F Martin
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Aug 12, 2006·The Journal of Organic Chemistry·Alexander DeitersStephen F Martin
Nov 2, 2007·The Journal of Organic Chemistry·Brandon L AshfeldStephen F Martin

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Citations

Nov 26, 2013·Journal of Asian Natural Products Research·Bing-Jie ZhangXiang-Hai Cai
Sep 15, 2010·Natural Product Reports·Minoru IshikuraTakumi Abe
Sep 12, 2014·Journal of the American Chemical Society·Zhiguo BianStephen F Martin
Apr 22, 2016·Chemical Reviews·Svilen P SimeonovCarlos A M Afonso
May 24, 2014·Journal of the American Chemical Society·David R Williams, Akshay A Shah
Oct 11, 2016·Chemical Communications : Chem Comm·Pei-Qiang HuangFeng Han
Jun 3, 2017·The Journal of Organic Chemistry·James D FirthLeigh Ferris
Jul 25, 2017·The Journal of Organic Chemistry·Stephen F Martin
Aug 1, 2020·Beilstein Journal of Organic Chemistry·Jorge EscorihuelaSantos Fustero
Sep 4, 2013·Chemical Communications : Chem Comm·Donald CraigAndrew J P White
Apr 29, 2021·Organic & Biomolecular Chemistry·Hiroaki Ohno, Shinsuke Inuki
Apr 10, 2019·The Journal of Organic Chemistry·Youssouf SanogoGeoffroy Sorin

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