کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5224378 1383516 2008 17 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
The Pauson–Khand reaction as a new entry to the synthesis of bridged bicyclic heterocycles: application to the enantioselective total synthesis of (−)-alstonerine
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
The Pauson–Khand reaction as a new entry to the synthesis of bridged bicyclic heterocycles: application to the enantioselective total synthesis of (−)-alstonerine
چکیده انگلیسی

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 alkaloid (−)-alstonerine.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 64, Issue 29, 14 July 2008, Pages 6884–6900