Journal
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Volume -, Issue 14, Pages 2277-2281Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b001114m
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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.
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