Extending pummerer reaction chemistry. Application to the total synthesis of (±)-dibromoagelaspongin

Ken S. Feldman; Matthew D. Fodor

doi:10.1021/ja807020d

Extending pummerer reaction chemistry. Application to the total synthesis of (±)-dibromoagelaspongin

Ken S. Feldman, Matthew D. Fodor

Chemistry

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41 Scopus citations

Abstract

The sponge metabolite dibromoagelaspongin was synthesized in 16 steps from imidazole. The route features two successive oxidative cyclizations with complete control of regiochemistry to deliver the unusual triaminomethane core of the target. These oxidative cyclizations likely resulted from Pummerer-like processes on the imidazole-2-sulfoxide (sulfide) precursors.

Original language	English (US)
Pages (from-to)	14964-14965
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	45
DOIs	https://doi.org/10.1021/ja807020d
State	Published - Nov 12 2008

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja807020d

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title = "Extending pummerer reaction chemistry. Application to the total synthesis of (±)-dibromoagelaspongin",

abstract = "The sponge metabolite dibromoagelaspongin was synthesized in 16 steps from imidazole. The route features two successive oxidative cyclizations with complete control of regiochemistry to deliver the unusual triaminomethane core of the target. These oxidative cyclizations likely resulted from Pummerer-like processes on the imidazole-2-sulfoxide (sulfide) precursors.",

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AU - Fodor, Matthew D.

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Y1 - 2008/11/12

N2 - The sponge metabolite dibromoagelaspongin was synthesized in 16 steps from imidazole. The route features two successive oxidative cyclizations with complete control of regiochemistry to deliver the unusual triaminomethane core of the target. These oxidative cyclizations likely resulted from Pummerer-like processes on the imidazole-2-sulfoxide (sulfide) precursors.

AB - The sponge metabolite dibromoagelaspongin was synthesized in 16 steps from imidazole. The route features two successive oxidative cyclizations with complete control of regiochemistry to deliver the unusual triaminomethane core of the target. These oxidative cyclizations likely resulted from Pummerer-like processes on the imidazole-2-sulfoxide (sulfide) precursors.

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JF - Journal of the American Chemical Society

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ER -

Extending pummerer reaction chemistry. Application to the total synthesis of (±)-dibromoagelaspongin

Abstract

All Science Journal Classification (ASJC) codes

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