Formal synthesis of (-)-aphanorphine using sequential photomediated radical reactions of dithiocarbamates

Richard Grainger; Emma Welsh

doi:10.1002/anie.200701055

Formal synthesis of (-)-aphanorphine using sequential photomediated radical reactions of dithiocarbamates

Richard Grainger, Emma Welsh

Chemistry

Research output: Contribution to journal › Article

70 Citations (Scopus)

Abstract

Time to change the light bulb: An alkyl dithiocarbamate, itself formed through a photoinitiated group-transfer cyclization of a carbamoyl radical, undergoes a second photomediated radical process initiated with a different light source. These two reactions, which proceed through the same cyclohexenyl radical intermediate, are key steps in a new asymmetric synthesis of the alkaloid aphanorphine. TEMPO=2,2,6,6-tetramethyl-1-piperidinoxyl radical.

Original language	English
Pages (from-to)	5377-5380
Journal	Angewandte Chemie (International Edition)
Volume	46
Issue number	28
DOIs	https://doi.org/10.1002/anie.200701055
Publication status	Published - 2 Jul 2007

Keywords

sulfinamides
cyclization
oxidation
radical reactions
metathesis

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10.1002/anie.200701055Licence: None: All rights reserved

Advanced Research Fellowship: Harnessing Reactive Intermediates for Organic Synthesis
Grainger, R. (Principal Investigator)
Engineering & Physical Science Research Council
1/09/05 → 31/08/10
Project: Research Councils

Cite this

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title = "Formal synthesis of (-)-aphanorphine using sequential photomediated radical reactions of dithiocarbamates",

abstract = "Time to change the light bulb: An alkyl dithiocarbamate, itself formed through a photoinitiated group-transfer cyclization of a carbamoyl radical, undergoes a second photomediated radical process initiated with a different light source. These two reactions, which proceed through the same cyclohexenyl radical intermediate, are key steps in a new asymmetric synthesis of the alkaloid aphanorphine. TEMPO=2,2,6,6-tetramethyl-1-piperidinoxyl radical.",

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AB - Time to change the light bulb: An alkyl dithiocarbamate, itself formed through a photoinitiated group-transfer cyclization of a carbamoyl radical, undergoes a second photomediated radical process initiated with a different light source. These two reactions, which proceed through the same cyclohexenyl radical intermediate, are key steps in a new asymmetric synthesis of the alkaloid aphanorphine. TEMPO=2,2,6,6-tetramethyl-1-piperidinoxyl radical.

KW - sulfinamides

KW - cyclization

KW - oxidation

KW - radical reactions

KW - metathesis

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DO - 10.1002/anie.200701055

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ER -

Formal synthesis of (-)-aphanorphine using sequential photomediated radical reactions of dithiocarbamates

Abstract

Keywords

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Projects

Advanced Research Fellowship: Harnessing Reactive Intermediates for Organic Synthesis

Cite this