Asymmetric Total Synthesis of (-)-Erogorgiaene and Its C-11 Epimer and Investigation of Their Antimycobacterial Activity

作者：Incerti Pradillos Celia A; Kabeshov Mikhail A; O'Hora Paul S; Shipilovskikh Sergei A; Rubtsov Aleksandr E; Drobkova Vera A; Balandina Svetlana Yu; Malkov Andrei V^*

来源：Chemistry - A European Journal, 2016, 22(40): 14390-14396.

DOI：10.1002/chem.201602440

• allylation
• asymmetric catalysis
• enantioselectivity
• rearrangement
• total synthesis

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 cat-ionic cyclisation. (-)-Erogorgiaene exhibited promising antitubercular activity against multidrug-resistant strains of Mycobacterium tuberculosis.

• 出版日期2016-9