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New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (±)-cinnamolide and (±)-methylenolactocin

✍ Scribed by Judith E Forbes; Radomir N Saicic; Samir Z Zard

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 810 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)01184-3

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✦ Synopsis

Irradiation with visible light of S-alkoxycarbonyl xanthates derived from various alcohols gives rise to alkoxycarbonyl radicals with bifurcate reactivity: loss of carbon dioxide leads to deoxygenated derivatives (i.e. alkyl xanthates) whereas intramolecular addition to a suitably located double bond produces lactones; these new reactions were applied to the total synthesis of (_+)-cinnamolide and (+)-methylenolactocin.

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