Tetrahedron

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

JE Forbes, RN Saicic, SZ Zard

文献索引：Forbes, Judith E.; Saicic, Radomir N.; Zard, Samir Z. Tetrahedron, 1999 , vol. 55, # 12 p. 3791 - 3802

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被引用次数: 35

摘要

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 (ie 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.