Asymmetric Total Synthesis of (-)-Erogorgiaene and Its C-11 Epimer and Investigation of Their Antimycobacterial Activity
Asymmetric Total Synthesis of (-)-Erogorgiaene and Its C-11 Epimer and Investigation of Their Antimycobacterial Activity
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DOI：
10.1002/chem.201602440
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发表时间：
2016-09-01
影响因子：
4.3
通讯作者：
Malkov, Andrei V.
中科院分区：
文献类型：
--
作者：
Incerti-Pradillos, Celia A.;Kabeshov, Mikhail A.;Malkov, Andrei V.
报道了一种短的、九步、高对映选择性合成（-）-毛蕊花烯及其C-11差向异构体的方法。关键的立体化学控制步骤包括催化不对称巴豆酰化、阴离子氧代Cope重排和阳离子环化。（-）-Erogorgiaene对结核分枝杆菌的多药耐药菌株表现出有希望的抗结核活性。
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.