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, DOI: 10.1002/chem.201602440.
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.
This paper is embargoed until August 2017.
The authors thank Russian Science Foundation for grant 15-13-00092 and the Loughborough University for studentships to CAIP and PSOH.