Asymmetric total synthesis of (-)-erogorgiaene and its C11 epimer and investigation of their antimycobacterial activity

Incerti-Pradillos, Celia A.; Kabeshov, Mikhail A.; O'Hora, Paul; Shipilovskikh, Sergei A.; Rubtsov, Aleksandr E.; Drobkova, Vera A.; Balandina, Svetlana Yu; Malkov, Andrei

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 Malkov

A 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 Journal

Pages

? - ? (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

Version

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

2016-06-27

Publication date

2016

Notes

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.