Exploration of the interrupted Fischer indolization reaction

TETRAHEDRON

卷:66

Article

Schammel, Alex W.¹  Boal, Ben W.¹  Zu, Liansuo¹  Mesganaw, Tehetena¹  Garg, Neil K.¹ 

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

关键词: Indoline;    Natural products;    Fischer indole synthesis;    Total synthesis;    Heterocycles;   

DOI  :  10.1016/j.tet.2010.02.050

来源: Elsevier

【 摘 要 】

A convergent method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. The method is convergent, mild, operationally simple, broad in scope, and can be used to access enantioenriched products. In addition, our approach is amenable to the synthesis of furoindoline and pyrrolidinoindoline natural products as demonstrated by the concise formal total syntheses of physovenine and debromoflustramine B. The strategy will likely enable the synthesis of more complex targets such as the communesin alkaloids. Published by Elsevier Ltd.

【 授权许可】

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