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Title: Asymmetric total synthesis of (-)-erogorgiaene and its C11 epimer and investigation of their antimycobacterial activity
Authors: Incerti-Pradillos, Celia A.
Kabeshov, Mikhail A.
O'Hora, Paul
Shipilovskikh, Sergei A.
Rubtsov, Aleksandr E.
Drobkova, Vera A.
Balandina, Svetlana Yu
Malkov, Andrei V.
Keywords: Allylation
Asymmetric catalysis
Total synthesis
Issue Date: 2016
Publisher: © Wiley
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.
Abstract: 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.
Description: This paper is embargoed until August 2017.
Sponsor: The authors thank Russian Science Foundation for grant 15-13-00092 and the Loughborough University for studentships to CAIP and PSOH.
Version: Accepted for publication
DOI: 10.1002/chem.201602440
URI: https://dspace.lboro.ac.uk/2134/22370
Publisher Link: http://dx.doi.org/10.1002/chem.201602440
ISSN: 0947-6539
Appears in Collections:Closed Access (Chemistry)

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