期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 21, 页码 7262-7267出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600273
关键词
4,5,6,7-tetrahydroindoles; alkaloids; green chemistry; thermally induced cyclization; total synthesis
资金
- Russian Foundation for Basic Research (RFBR), Russia [14-03-31685, 14-03-01114]
A facile one-pot approach based on a thermally induced metal-and solvent-free 5-endo-dig cyclization reaction of the amino propargylic alcohols in combination with Dess-Martin periodinane-promoted oxidative dearomatization of 4,5,6,7-tetrahydroindole intermediates provides an efficient and robust access to 5,6-dihydro-1H-indol-2(4H)ones. Green, relatively mild and operationally simple characteristics of the synthetic sequence are the major advantages, which greatly amplify the developed methodology. The utility of obtained indolones as unified key precursors is demonstrated by the application of these products to the formal total syntheses of a whole pleiad of Erythrina-and Lycorine-type alkaloids, namely (+/-)-erysotramidine, (+/-)-erysotrine, (+/-)-erythravine, (+/-)-gamma-lycorane, and abnormal erythrinanes (+/-)-coccoline and (+/-)-coccuvinine.
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