volume 15 issue 22 pages 5790-5793

Scalable and Divergent Total Synthesis of (+)-Colletoic Acid, a Selective 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitor

Publication typeJournal Article
Publication date2013-11-01
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
PubMed ID:  24175735
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
An efficient and divergent total synthesis of (+)-colletoic acid, a selective 11-β hydroxysteroid dehydrogenase 1 (11-βHSD1) inhibitor, is presented along with its biological activity at the whole-cell level. A scalable, asymmetric synthetic strategy was designed featuring a diversity-oriented synthesis utilizing a diastereoselective intramolecular 5-exo-Heck reaction as the key step to provide the quaternary spirocenter intermediate 9 in multigram scale, thus establishing a platform for further structure-activity relationship studies and providing access to other acorane family members.
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GOST |
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GOST Copy
Ling T. et al. Scalable and Divergent Total Synthesis of (+)-Colletoic Acid, a Selective 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitor // Organic Letters. 2013. Vol. 15. No. 22. pp. 5790-5793.
GOST all authors (up to 50) Copy
Ling T., Griffith E., Mitachi K., Rivas F. Scalable and Divergent Total Synthesis of (+)-Colletoic Acid, a Selective 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitor // Organic Letters. 2013. Vol. 15. No. 22. pp. 5790-5793.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/ol402842u
UR - https://doi.org/10.1021/ol402842u
TI - Scalable and Divergent Total Synthesis of (+)-Colletoic Acid, a Selective 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitor
T2 - Organic Letters
AU - Ling, Taotao
AU - Griffith, Elizabeth
AU - Mitachi, Katsuhiko
AU - Rivas, Fatima
PY - 2013
DA - 2013/11/01
PB - American Chemical Society (ACS)
SP - 5790-5793
IS - 22
VL - 15
PMID - 24175735
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2013_Ling,
author = {Taotao Ling and Elizabeth Griffith and Katsuhiko Mitachi and Fatima Rivas},
title = {Scalable and Divergent Total Synthesis of (+)-Colletoic Acid, a Selective 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitor},
journal = {Organic Letters},
year = {2013},
volume = {15},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/ol402842u},
number = {22},
pages = {5790--5793},
doi = {10.1021/ol402842u}
}
MLA
Cite this
MLA Copy
Ling, Taotao, et al. “Scalable and Divergent Total Synthesis of (+)-Colletoic Acid, a Selective 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitor.” Organic Letters, vol. 15, no. 22, Nov. 2013, pp. 5790-5793. https://doi.org/10.1021/ol402842u.