New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (+/-)-cinnamolide and (+/-)-metlhylenolactocin
Abstract
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, 3791-3802Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
DOI: 10.1016/S0040-4020(98)01184-3
ISSN: 0040-4020
WoS: 000079099800027
Scopus: 2-s2.0-0033583016
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Forbes, JE AU - Saičić, Radomir AU - Zard, SZ PY - 1999 UR - https://cherry.chem.bg.ac.rs/handle/123456789/409 AB - 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. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Tetrahedron T1 - New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (+/-)-cinnamolide and (+/-)-metlhylenolactocin VL - 55 IS - 12 SP - 3791 EP - 3802 DO - 10.1016/S0040-4020(98)01184-3 ER -
@article{ author = "Forbes, JE and Saičić, Radomir and Zard, SZ", year = "1999", abstract = "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.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Tetrahedron", title = "New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (+/-)-cinnamolide and (+/-)-metlhylenolactocin", volume = "55", number = "12", pages = "3791-3802", doi = "10.1016/S0040-4020(98)01184-3" }
Forbes, J., Saičić, R.,& Zard, S.. (1999). New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (+/-)-cinnamolide and (+/-)-metlhylenolactocin. in Tetrahedron Pergamon-Elsevier Science Ltd, Oxford., 55(12), 3791-3802. https://doi.org/10.1016/S0040-4020(98)01184-3
Forbes J, Saičić R, Zard S. New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (+/-)-cinnamolide and (+/-)-metlhylenolactocin. in Tetrahedron. 1999;55(12):3791-3802. doi:10.1016/S0040-4020(98)01184-3 .
Forbes, JE, Saičić, Radomir, Zard, SZ, "New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (+/-)-cinnamolide and (+/-)-metlhylenolactocin" in Tetrahedron, 55, no. 12 (1999):3791-3802, https://doi.org/10.1016/S0040-4020(98)01184-3 . .