New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (+/-)-cinnamolide and (+/-)-metlhylenolactocin
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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. (C) 1999 Elsevier Science Ltd. All rights reserved.
Source:Tetrahedron, 1999, 55, 12, 3791-3802
- Pergamon-Elsevier Science Ltd, Oxford