Asymmetric total synthesis of (-)-erogorgiaene and its C11 epimer and investigation of their antimycobacterial activity
journal contributionposted on 07.09.2016 by Celia A. Incerti-Pradillos, Mikhail A. Kabeshov, Paul O'Hora, Sergei A. Shipilovskikh, Aleksandr E. Rubtsov, Vera A. Drobkova, Svetlana Yu Balandina, Andrei Malkov
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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.
The authors thank Russian Science Foundation for grant 15-13-00092 and the Loughborough University for studentships to CAIP and PSOH.