A General Approach to the Asymmetric Synthesis of Lignans: (-)-Methyl Piperitol, (-)-Sesamin, (-)-Aschantin, (+)-Yatein, (+)-Dihydroclusin, (+)-Burseran, and (-)-Isostegane
Publication type: Journal Article
Publication date: 2002-07-26
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
A highly efficient, diastereo- and enantioselective route was developed to access a great variety of lignans. The asymmetric synthesis of the 2,3-disubstituted γ-butyrolactones 9a-c could be improved in the case of aldol reactions by employing 2.2 equivalents of LiCl as an additive to provide, after purification, highly diastereo- and enantioenriched starting materials for the synthesis of the furofuran lignans (-)-methyl piperitol, (-)-sesamin, and (-)-aschantin. Furthermore, the γ-butyrolactone 15 was converted into dibenzylbutyrolactone lignan (+)-yatein, the dibenzylbutandiol type (+)-dihydroclusin, the tetrahydrofuran type (+)-burseran, and the dibenzocyclooctadiene type (-)-isostegane.
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Enders D. et al. A General Approach to the Asymmetric Synthesis of Lignans: (-)-Methyl Piperitol, (-)-Sesamin, (-)-Aschantin, (+)-Yatein, (+)-Dihydroclusin, (+)-Burseran, and (-)-Isostegane // Synthesis. 2002. Vol. 2002. No. 04. pp. 515-522.
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Enders D., Lausberg V., Signore G. D., Berner O. M. A General Approach to the Asymmetric Synthesis of Lignans: (-)-Methyl Piperitol, (-)-Sesamin, (-)-Aschantin, (+)-Yatein, (+)-Dihydroclusin, (+)-Burseran, and (-)-Isostegane // Synthesis. 2002. Vol. 2002. No. 04. pp. 515-522.
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TY - JOUR
DO - 10.1055/s-2002-20967
UR - https://doi.org/10.1055/s-2002-20967
TI - A General Approach to the Asymmetric Synthesis of Lignans: (-)-Methyl Piperitol, (-)-Sesamin, (-)-Aschantin, (+)-Yatein, (+)-Dihydroclusin, (+)-Burseran, and (-)-Isostegane
T2 - Synthesis
AU - Enders, D.
AU - Lausberg, Vivien
AU - Signore, Giuseppe Del
AU - Berner, Otto Mathias
PY - 2002
DA - 2002/07/26
PB - Georg Thieme Verlag KG
SP - 515-522
IS - 04
VL - 2002
SN - 0039-7881
SN - 1437-210X
ER -
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BibTex (up to 50 authors)
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@article{2002_Enders,
author = {D. Enders and Vivien Lausberg and Giuseppe Del Signore and Otto Mathias Berner},
title = {A General Approach to the Asymmetric Synthesis of Lignans: (-)-Methyl Piperitol, (-)-Sesamin, (-)-Aschantin, (+)-Yatein, (+)-Dihydroclusin, (+)-Burseran, and (-)-Isostegane},
journal = {Synthesis},
year = {2002},
volume = {2002},
publisher = {Georg Thieme Verlag KG},
month = {jul},
url = {https://doi.org/10.1055/s-2002-20967},
number = {04},
pages = {515--522},
doi = {10.1055/s-2002-20967}
}
Cite this
MLA
Copy
Enders, D., et al. “A General Approach to the Asymmetric Synthesis of Lignans: (-)-Methyl Piperitol, (-)-Sesamin, (-)-Aschantin, (+)-Yatein, (+)-Dihydroclusin, (+)-Burseran, and (-)-Isostegane.” Synthesis, vol. 2002, no. 04, Jul. 2002, pp. 515-522. https://doi.org/10.1055/s-2002-20967.