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

56 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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10.1016/S0040-4039(00)00194-5

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

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.",

author = "Xichen Lin and Didier Stien and Weinreb, \{Steven M.\}",

note = "Funding Information: We are grateful to the National Institutes of Health (CA-34303) for financial support of this research and the Ministry of Foreign Affairs (France) for a Lavoisier Postdoctoral Fellowship to D.S. We thank Professor J. Rigby for providing copies of spectra of the alcohol epimer of 17 for comparison purposes. We are also grateful to Professor H. Hiemstra for NMR spectra of authentic alcohol 17 and its acetate derivative which confirmed the structure and stereochemistry of our material.",

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doi = "10.1016/S0040-4039(00)00194-5",

language = "English (US)",

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T1 - A mild new procedure for production, cyclization and trapping of amidyl radicals

T2 - Application to a formal total synthesis of peduncularine

AU - Lin, Xichen

AU - Stien, Didier

AU - Weinreb, Steven M.

N1 - Funding Information: We are grateful to the National Institutes of Health (CA-34303) for financial support of this research and the Ministry of Foreign Affairs (France) for a Lavoisier Postdoctoral Fellowship to D.S. We thank Professor J. Rigby for providing copies of spectra of the alcohol epimer of 17 for comparison purposes. We are also grateful to Professor H. Hiemstra for NMR spectra of authentic alcohol 17 and its acetate derivative which confirmed the structure and stereochemistry of our material.

PY - 2000/4/1

Y1 - 2000/4/1

N2 - 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.

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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U2 - 10.1016/S0040-4039(00)00194-5

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

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

Abstract

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