(+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity
Graziela G Bianco
1
,
Helena M.C Ferraz
1
,
Arinice M Costa
1
,
Letícia V. Costa-Lotufo
1
,
Cláudia Pessoa
1
,
Manoel O. de Moraes
1
,
Marcus G Schrems
1
,
A. Pfaltz
1
,
Luiz C. Silva
1
Publication type: Journal Article
Publication date: 2009-02-20
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
19231874
Organic Chemistry
Abstract
The first synthesis of the natural product (+)-mutisianthol was accomplished in 11 steps and in 21% overall yield from 2-methylanisole. The synthesis of its enantiomer was also performed in a similar overall yield. The absolute configuration of the sesquiterpene (+)-mutisianthol was assigned as (1S,3R). Key steps in the route are the asymmetric hydrogenation of a nonfunctionalized olefin using chiral iridium catalysts and the ring contraction of 1,2-dihydronaphthalenes using thallium(III) or iodine(III). The target molecules show moderate activity against the human tumor cell lines SF-295, HCT-8, and MDA-MB-435.
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84
Total citations:
84
Citations from 2024:
5
(5.95%)
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GOST
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Bianco G. G. et al. (+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity // Journal of Organic Chemistry. 2009. Vol. 74. No. 6. pp. 2561-2566.
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Bianco G. G., Ferraz H. M., Costa A. M., Costa-Lotufo L. V., Pessoa C., de Moraes M. O., Schrems M. G., Pfaltz A., Silva L. C. (+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity // Journal of Organic Chemistry. 2009. Vol. 74. No. 6. pp. 2561-2566.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo9000405
UR - https://doi.org/10.1021/jo9000405
TI - (+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity
T2 - Journal of Organic Chemistry
AU - Bianco, Graziela G
AU - Ferraz, Helena M.C
AU - Costa, Arinice M
AU - Costa-Lotufo, Letícia V.
AU - Pessoa, Cláudia
AU - de Moraes, Manoel O.
AU - Schrems, Marcus G
AU - Pfaltz, A.
AU - Silva, Luiz C.
PY - 2009
DA - 2009/02/20
PB - American Chemical Society (ACS)
SP - 2561-2566
IS - 6
VL - 74
PMID - 19231874
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2009_Bianco,
author = {Graziela G Bianco and Helena M.C Ferraz and Arinice M Costa and Letícia V. Costa-Lotufo and Cláudia Pessoa and Manoel O. de Moraes and Marcus G Schrems and A. Pfaltz and Luiz C. Silva},
title = {(+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity},
journal = {Journal of Organic Chemistry},
year = {2009},
volume = {74},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/jo9000405},
number = {6},
pages = {2561--2566},
doi = {10.1021/jo9000405}
}
Cite this
MLA
Copy
Bianco, Graziela G., et al. “(+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity.” Journal of Organic Chemistry, vol. 74, no. 6, Feb. 2009, pp. 2561-2566. https://doi.org/10.1021/jo9000405.