The asymmetric synthesis of aryltetralin lignans: (−)-isolariciresinol dimethyl ether and (−)-deoxysikkimotoxin
Тип публикации: Journal Article
Дата публикации: 1996-01-01
scimago Q3
wos Q4
БС3
SJR: 0.254
CiteScore: 2
Impact factor: 1
ISSN: 00084042, 14803291
General Chemistry
Catalysis
Organic Chemistry
Краткое описание
The total asymmetric syntheses of (−)-isolariciresinol dimethyl ether (6) and (−)-deoxysikkimotoxin (7) have been carried out, in an attempt to exploit a synthetic strategy recently developed for the synthesis of (−)-deoxypodophyllotoxin (1, R1 = -CH2−, Ar = 3,4,5-trimethoxyphenyl). In so doing, a generalized method for the synthesis of aryltetralin lignans has been developed that should be applicable to a variety of substitution patterns and stereochemistries. A one-pot, 100% regio-selective reduction–lactonization procedure has been developed for the conversion of the ester 18b to (−)-deoxysikkimotoxin, which gave 93% isolated yield in that step. Key words: ortho-quinodimethanes, lignans, Diels–Alder, asymmetric, mandelate.
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Coltart D. M., Charlton J. L. The asymmetric synthesis of aryltetralin lignans: (−)-isolariciresinol dimethyl ether and (−)-deoxysikkimotoxin // Canadian Journal of Chemistry. 1996. Vol. 74. No. 1. pp. 88-94.
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Coltart D. M., Charlton J. L. The asymmetric synthesis of aryltetralin lignans: (−)-isolariciresinol dimethyl ether and (−)-deoxysikkimotoxin // Canadian Journal of Chemistry. 1996. Vol. 74. No. 1. pp. 88-94.
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TY - JOUR
DO - 10.1139/v96-011
UR - https://doi.org/10.1139/v96-011
TI - The asymmetric synthesis of aryltetralin lignans: (−)-isolariciresinol dimethyl ether and (−)-deoxysikkimotoxin
T2 - Canadian Journal of Chemistry
AU - Coltart, Don M.
AU - Charlton, James L
PY - 1996
DA - 1996/01/01
PB - Canadian Science Publishing
SP - 88-94
IS - 1
VL - 74
SN - 0008-4042
SN - 1480-3291
ER -
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BibTex (до 50 авторов)
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@article{1996_Coltart,
author = {Don M. Coltart and James L Charlton},
title = {The asymmetric synthesis of aryltetralin lignans: (−)-isolariciresinol dimethyl ether and (−)-deoxysikkimotoxin},
journal = {Canadian Journal of Chemistry},
year = {1996},
volume = {74},
publisher = {Canadian Science Publishing},
month = {jan},
url = {https://doi.org/10.1139/v96-011},
number = {1},
pages = {88--94},
doi = {10.1139/v96-011}
}
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MLA
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Coltart, Don M., and James L Charlton. “The asymmetric synthesis of aryltetralin lignans: (−)-isolariciresinol dimethyl ether and (−)-deoxysikkimotoxin.” Canadian Journal of Chemistry, vol. 74, no. 1, Jan. 1996, pp. 88-94. https://doi.org/10.1139/v96-011.