Structure and Absolute Configuration of Nyasol and Hinokiresinol via Synthesis and Vibrational Circular Dichroism Spectroscopy
Peter R Lassen
1
,
Dorthe Mondrup Skytte
1
,
LARS HEMMINGSEN
1
,
Simon Feldbæk Nielsen
1
,
Teresa B Freedman
1
,
Laurence A. Nafie
1
,
S.B. Christensen
1
Publication type: Journal Article
Publication date: 2005-10-21
scimago Q1
wos Q1
SJR: 0.629
CiteScore: 6.5
Impact factor: 3.6
ISSN: 01633864, 15206025
PubMed ID:
16309307
Organic Chemistry
Drug Discovery
Pharmacology
Pharmaceutical Science
Molecular Medicine
Complementary and alternative medicine
Analytical Chemistry
Abstract
The absolute configuration of the norlignan (+)-nyasol was determined to be S by comparison of the experimental vibrational circular dichroism data with first-principle calculations taking into account the eight lowest energy conformations. The established absolute configuration of (+)-nyasol enables establishment of the absolute configuration of (-)-hinokiresinol, which is concluded to be S. A total synthesis and resolution of hinokiresinol has been performed to resolve the conflicting reports of the coupling constant of the vinylic protons of the disubstituted double bond in this molecule. Racemic hinokiresinol was resolved. Both enantiomers possess the same antiplasmodial activity.
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29
Total citations:
29
Citations from 2024:
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(10%)
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MLA
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GOST
Copy
Lassen P. R. et al. Structure and Absolute Configuration of Nyasol and Hinokiresinol via Synthesis and Vibrational Circular Dichroism Spectroscopy // Journal of Natural Products. 2005. Vol. 68. No. 11. pp. 1603-1609.
GOST all authors (up to 50)
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Lassen P. R., Skytte D. M., HEMMINGSEN L., Nielsen S. F., Freedman T. B., Nafie L. A., Christensen S. Structure and Absolute Configuration of Nyasol and Hinokiresinol via Synthesis and Vibrational Circular Dichroism Spectroscopy // Journal of Natural Products. 2005. Vol. 68. No. 11. pp. 1603-1609.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/np0502995
UR - https://doi.org/10.1021/np0502995
TI - Structure and Absolute Configuration of Nyasol and Hinokiresinol via Synthesis and Vibrational Circular Dichroism Spectroscopy
T2 - Journal of Natural Products
AU - Lassen, Peter R
AU - Skytte, Dorthe Mondrup
AU - HEMMINGSEN, LARS
AU - Nielsen, Simon Feldbæk
AU - Freedman, Teresa B
AU - Nafie, Laurence A.
AU - Christensen, S.B.
PY - 2005
DA - 2005/10/21
PB - American Chemical Society (ACS)
SP - 1603-1609
IS - 11
VL - 68
PMID - 16309307
SN - 0163-3864
SN - 1520-6025
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2005_Lassen,
author = {Peter R Lassen and Dorthe Mondrup Skytte and LARS HEMMINGSEN and Simon Feldbæk Nielsen and Teresa B Freedman and Laurence A. Nafie and S.B. Christensen},
title = {Structure and Absolute Configuration of Nyasol and Hinokiresinol via Synthesis and Vibrational Circular Dichroism Spectroscopy},
journal = {Journal of Natural Products},
year = {2005},
volume = {68},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/np0502995},
number = {11},
pages = {1603--1609},
doi = {10.1021/np0502995}
}
Cite this
MLA
Copy
Lassen, Peter R., et al. “Structure and Absolute Configuration of Nyasol and Hinokiresinol via Synthesis and Vibrational Circular Dichroism Spectroscopy.” Journal of Natural Products, vol. 68, no. 11, Oct. 2005, pp. 1603-1609. https://doi.org/10.1021/np0502995.