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

Judith E. Forbes; Radomir N. Saicic; Samir Z. Zard

doi:10.1016/S0040-4020(98)01184-3

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

Judith E. Forbes
, Radomir N. Saicic
, Samir Z. Zard

Centre national de la recherche scientifique
Laboratoire de Synthèse Organique

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3791-3802
Number of pages	12
Journal	Tetrahedron
Volume	55
Issue number	12
DOIs	https://doi.org/10.1016/S0040-4020(98)01184-3
Publication status	Published - 19 Mar 1999

Keywords

Lactones
Radical reactions
Terpenes
Xanthates

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10.1016/S0040-4020(98)01184-3

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

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.",

keywords = "Lactones, Radical reactions, Terpenes, Xanthates",

author = "Forbes, \{Judith E.\} and Saicic, \{Radomir N.\} and Zard, \{Samir Z.\}",

year = "1999",

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doi = "10.1016/S0040-4020(98)01184-3",

language = "English",

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T1 - New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (±)-cinnamolide and (±)-methylenolactocin

AU - Forbes, Judith E.

AU - Saicic, Radomir N.

AU - Zard, Samir Z.

PY - 1999/3/19

Y1 - 1999/3/19

N2 - 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.

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.

KW - Lactones

KW - Radical reactions

KW - Terpenes

KW - Xanthates

U2 - 10.1016/S0040-4020(98)01184-3

DO - 10.1016/S0040-4020(98)01184-3

M3 - Article

AN - SCOPUS:0033583016

SN - 0040-4020

VL - 55

SP - 3791

EP - 3802

JO - Tetrahedron

JF - Tetrahedron

IS - 12

ER -

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

Abstract

Keywords

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