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

被引：15

作者：

Cocquet, G ^{[1
]}

Rool, P ^{[1
]}

Ferroud, C ^{[1
]}

机构：

[1] Conservatoire Natl Arts & Metiers, CNRS, Chim Organ Lab, F-75141 Paris 03, France

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 14期

关键词：

D O I：

10.1039/b001114m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 (+)-3 beta-cyanocatharanthine 3 and the new (-)-16-O-acetyl-3 alpha-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.

引用

页码：2277 / 2281

页数：5

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