期刊
TETRAHEDRON
卷 65, 期 16, 页码 3222-3231出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.10.074
关键词
Iminium ion; Cascade reaction; Alkaloid synthesis; Stereoselective
资金
- NIGMS NIH HHS [R01 GM025439, R01 GM025439-24A2, R01 GM025439-26, R01 GM025439-25] Funding Source: Medline
A novel iminium ion cascade reaction has been developed that allows for the steteoselective synthesis of a variety Of Substituted aza-fused bicycles- The combination of amino allylsilanes and aldehydes (or ketones) was used to synthesize a number of quinolizidines and indolizidines in a one-pot reaction sequence. This technology has been used to effect the facile syntheses of several indolizidine and quinolizidine natural product including (+/-)-epilupinine, (+/-)-tashirornine, and (-)-epimyrtine. Substrate scope has been examined varying the type of amino allylsilanes (primary, secondary, and conjugated) and carbonyl compounds (aldehydes and ketones) to give a variety of fused ring structures. Varying the components chosen allows for the inclusion of synthetically useful functional groups at different positions on the core structure. The methodology has been Used to construct the tricyclic Core Structures present in the cylindricine family and halichlorine. (C) 2008 Elsevier Ltd. All Fights reserved.
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