Issue 14, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Photosensitized oxidation, by single-electron transfer, of catharanthine and vindoline: a highly regio- and diastereoselective photocyanation reaction

Guillaume Cocquet,a   Patrice Roola  and  Clotilde Ferroud*a  

* Corresponding authors

a Laboratoire de Chimie Organique associé au CNRS, Conservatoire National des Arts et Métiers, 292, rue Saint Martin, Paris Cedex 03, France

Abstract

The irradiation, by visible light, of (+)-catharanthine 1 and of (−)-16-O-acetylvindoline 5 in the presence of cyanide ion and a catalytic amount of a photosensitizer known to produce singlet oxygen leads to (+)-3β-cyanocatharanthine 3 and the new (−)-16-O-acetyl-3α-cyanovindoline 6. The complete stereostructural identification of these compounds has been ascertained by an accurate spectroscopic survey. High regio- and diastereoselectivities (de > 99%) are observed. Some experiments have been performed which confirm unambiguously that singlet oxygen is the oxidizing species in such photochemical conditions.

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Article information

DOI
https://doi.org/10.1039/B001114M
Article type
Paper
Submitted
09 Feb 2000
Accepted
02 Jun 2000
First published
30 Jun 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2277-2281

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Photosensitized oxidation, by single-electron transfer, of catharanthine and vindoline: a highly regio- and diastereoselective photocyanation reaction

G. Cocquet, P. Rool and C. Ferroud, J. Chem. Soc., Perkin Trans. 1, 2000, 2277 DOI: 10.1039/B001114M

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