Extending pummerer reaction chemistry: (±)-dibromoagelaspongin synthesis and related studies

Ken S. Feldman; Matthew D. Fodor

doi:10.1021/jo900283g

Extending pummerer reaction chemistry: (±)-dibromoagelaspongin synthesis and related studies

Ken S. Feldman, Matthew D. Fodor

Chemistry

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33 Scopus citations

Abstract

The sponge-derived alkaloid dibromoagelaspongin was prepared from a dihydrooroidin derivative by exploiting the Pummerer reaction twice in succession. Oxidative cyclization of the substrate's pyrrole-2-carboxamide function into the imidazole moiety was achieved in a regiospecific manner to establish both C-N bonds to C(6) of the target.

Original language	English (US)
Pages (from-to)	3449-3461
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	74
Issue number	9
DOIs	https://doi.org/10.1021/jo900283g
State	Published - May 1 2009

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo900283g

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title = "Extending pummerer reaction chemistry: (±)-dibromoagelaspongin synthesis and related studies",

abstract = "The sponge-derived alkaloid dibromoagelaspongin was prepared from a dihydrooroidin derivative by exploiting the Pummerer reaction twice in succession. Oxidative cyclization of the substrate's pyrrole-2-carboxamide function into the imidazole moiety was achieved in a regiospecific manner to establish both C-N bonds to C(6) of the target.",

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AU - Fodor, Matthew D.

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N2 - The sponge-derived alkaloid dibromoagelaspongin was prepared from a dihydrooroidin derivative by exploiting the Pummerer reaction twice in succession. Oxidative cyclization of the substrate's pyrrole-2-carboxamide function into the imidazole moiety was achieved in a regiospecific manner to establish both C-N bonds to C(6) of the target.

AB - The sponge-derived alkaloid dibromoagelaspongin was prepared from a dihydrooroidin derivative by exploiting the Pummerer reaction twice in succession. Oxidative cyclization of the substrate's pyrrole-2-carboxamide function into the imidazole moiety was achieved in a regiospecific manner to establish both C-N bonds to C(6) of the target.

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Extending pummerer reaction chemistry: (±)-dibromoagelaspongin synthesis and related studies

Abstract

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