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Exploration of the interrupted Fischer indolization reaction.

ABSTRACT: 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.

SUBMITTER: Schammel AW

PROVIDER: S-EPMC2925302 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Exploration of the interrupted Fischer indolization reaction.

Schammel Alex W AW Boal Ben W BW Zu Liansuo L Mesganaw Tehetena T Garg Neil K NK

Tetrahedron 20100601 26

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 furoindolin ...[more]

PMID: 20798890

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