Asymmetric Total Synthesis of (-)-Erogorgiaene and Its C-11 Epimer and Investigation of Their Antimycobacterial Activity.
Celia A Incerti-PradillosMikhail A KabeshovPaul S O'HoraSergei A ShipilovskikhAleksandr E RubtsovVera A DrobkovaSvetlana Yu BalandinaAndrei V MalkovPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2016)
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.