CEJ erogor-1k.pdf (433.91 kB)
Asymmetric total synthesis of (-)-erogorgiaene and its C11 epimer and investigation of their antimycobacterial activity
journal contribution
posted on 2016-09-07, 13:53 authored by Celia A. Incerti-Pradillos, Mikhail A. Kabeshov, Paul O'Hora, Sergei A. Shipilovskikh, Aleksandr E. Rubtsov, Vera A. Drobkova, Svetlana Yu Balandina, Andrei MalkovAndrei MalkovA short, nine-step, highly enantioselective synthesis of (−)-erogorgiaene and its C-11 epimer is reported. The key stereochemistry controlling steps involve catalytic asymmetric crotylation, anionic oxy-Cope rearrangement and cationic cyclisation. (−)-Erogorgiaene exhibited promising antitubercular activity against multidrug-resistant strains of Mycobacterium tuberculosis.
Funding
The authors thank Russian Science Foundation for grant 15-13-00092 and the Loughborough University for studentships to CAIP and PSOH.
History
School
- Science
Department
- Chemistry
Published in
Chemistry - A European JournalPages
? - ? (8)Citation
INCERTI-PRADILLOS, C.A. ... et al, 2016. Asymmetric total synthesis of (-)-erogorgiaene and its C11 epimer and investigation of their antimycobacterial activity. Chemistry - A European Journal, 22 (40), pp. 14390-14396.Publisher
© WileyVersion
- AM (Accepted Manuscript)
Publisher statement
This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/Acceptance date
2016-06-27Publication date
2016Notes
This is the peer reviewed version of the following article: INCERTI-PRADILLOS, C.A. ... et al, 2016. Asymmetric total synthesis of (-)-erogorgiaene and its C11 epimer and investigation of their antimycobacterial activity. Chemistry - A European Journal, 22 (40), pp. 14390-14396., which has been published in final form at http://dx.doi.org/10.1002/chem.201602440. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.ISSN
0947-6539Publisher version
Language
- en