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Protic-solvent-mediated cycloisomerization of quinoline and isoquinoline propargylic alcohols: syntheses of (±)-3-demethoxyerythratidinone and (±)-cocculidine.

ABSTRACT: Putting the "benz" in indolizinones: A cycloisomerization approach to benz[g]indolizinones and benz[e]indolizinones provides the first general route to these unique azacycles (see example). The utility of the benzindolizinone products was demonstrated by the application of this method to the total synthesis of the Erythrina alkaloids 3-demethoxyerythratidinone and cocculidine.

SUBMITTER: Heller ST

PROVIDER: S-EPMC4000449 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Protic-solvent-mediated cycloisomerization of quinoline and isoquinoline propargylic alcohols: syntheses of (±)-3-demethoxyerythratidinone and (±)-cocculidine.

Heller Stephen T ST Kiho Toshihiro T Narayan Alison R H AR Sarpong Richmond R

Angewandte Chemie (International ed. in English) 20130905 42

Putting the "benz" in indolizinones: A cycloisomerization approach to benz[g]indolizinones and benz[e]indolizinones provides the first general route to these unique azacycles (see example). The utility of the benzindolizinone products was demonstrated by the application of this method to the total synthesis of the Erythrina alkaloids 3-demethoxyerythratidinone and cocculidine. ...[more]

PMID: 24009078

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