Natural Furanocembranoids. A Synthetic Approach to Lophotoxin based on an Acyl Radical Macrocyclisation Strategy
Тип публикации: Journal Article
Дата публикации: 1992-01-01
SCImago Q2
WOS Q2
БС2
SJR: 0.443
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Краткое описание
A concise synthesis of the furan-containing macrocyclic (cembranoid) ring system 8 (10-isopropenyl-3,7,1 13-trimethyl-15-oxabicyclo[10.2.1] pentadeca-2,6,12,14-tetraene) found in lophotoxin (1) and other members of this family of irreversible nicotinic receptor antagonists, is described. The synthesis features a 14-endo trig cyclisation from an unsaturated acyl radical intermediate incor porating a terminal conjugated enone moiety, viz 10, leading to the macrocycle (5E,9E)-13-isopropenyl-2,6,10-trimethylcyclotetradeca-5,9-diene-2,4-dione (9), followed by acid-catalysed furan ring formation from the resulting 1,4-dione system in 9 (Scheme 1)
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Astley M. P., Pattenden G. Natural Furanocembranoids. A Synthetic Approach to Lophotoxin based on an Acyl Radical Macrocyclisation Strategy // Synthesis. 1992. Vol. 1992. No. 1/2. pp. 101-105.
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Astley M. P., Pattenden G. Natural Furanocembranoids. A Synthetic Approach to Lophotoxin based on an Acyl Radical Macrocyclisation Strategy // Synthesis. 1992. Vol. 1992. No. 1/2. pp. 101-105.
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TY - JOUR
DO - 10.1055/s-1992-34169
UR - https://doi.org/10.1055/s-1992-34169
TI - Natural Furanocembranoids. A Synthetic Approach to Lophotoxin based on an Acyl Radical Macrocyclisation Strategy
T2 - Synthesis
AU - Astley, Martin P
AU - Pattenden, G.
PY - 1992
DA - 1992/01/01
PB - Georg Thieme Verlag KG
SP - 101-105
IS - 1/2
VL - 1992
SN - 0039-7881
SN - 1437-210X
ER -
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BibTex (до 50 авторов)
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@article{1992_Astley,
author = {Martin P Astley and G. Pattenden},
title = {Natural Furanocembranoids. A Synthetic Approach to Lophotoxin based on an Acyl Radical Macrocyclisation Strategy},
journal = {Synthesis},
year = {1992},
volume = {1992},
publisher = {Georg Thieme Verlag KG},
month = {jan},
url = {https://doi.org/10.1055/s-1992-34169},
number = {1/2},
pages = {101--105},
doi = {10.1055/s-1992-34169}
}
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MLA
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Astley, Martin P., and G. Pattenden. “Natural Furanocembranoids. A Synthetic Approach to Lophotoxin based on an Acyl Radical Macrocyclisation Strategy.” Synthesis, vol. 1992, no. 1/2, Jan. 1992, pp. 101-105. https://doi.org/10.1055/s-1992-34169.
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