A mild new procedure for production, cyclization and trapping of amidyl radicals: Application to a formal total synthesis of peduncularine

Xichen Lin; Didier Stien; Steven M. Weinreb

doi:10.1016/S0040-4039(00)00194-5

A mild new procedure for production, cyclization and trapping of amidyl radicals: Application to a formal total synthesis of peduncularine

Xichen Lin, Didier Stien, Steven M. Weinreb

Chemistry

Research output: Contribution to journal › Article › peer-review

48 Scopus citations

Abstract

Treatment of an olefinic hydroxamic acid with tert-butylsulfinyl chloride and Hunig's base from -50°C to room temperature in the presence of a radical trap such as diphenyl diselenide, diphenyl disulfide or TEMPO affords a functionalized product derived from an amidyl radical cyclization. The methodology has been used in a formal total synthesis of the 6- azabicyclo[3.2.1]octane-containing indole alkaloid peduncularine. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	2333-2337
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(00)00194-5
State	Published - Apr 1 2000

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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AU - Lin, Xichen

AU - Stien, Didier

AU - Weinreb, Steven M.

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AB - Treatment of an olefinic hydroxamic acid with tert-butylsulfinyl chloride and Hunig's base from -50°C to room temperature in the presence of a radical trap such as diphenyl diselenide, diphenyl disulfide or TEMPO affords a functionalized product derived from an amidyl radical cyclization. The methodology has been used in a formal total synthesis of the 6- azabicyclo[3.2.1]octane-containing indole alkaloid peduncularine. (C) 2000 Elsevier Science Ltd.

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