期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 358, 期 3, 页码 444-451出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500781
关键词
amination; biocatalysis; biotransformations; pyrrolizidine alkaloids; transaminases; xenovenine
资金
- Austrian chamber of economy
The (+)- as well as the (-)-enantiomer of the pyrrolizidine alkaloid xenovenine were prepared within five steps with 17 and 30% overall yields, respectively, in optically pure form, >99% ee as well as >99% de. In the asymmetric key step a transaminase performed a regio- and stereoselective mono-amination of a triketone. By employing two enantio-complementary transaminases from Arthrobacter sp. both enantiomers were accessible. The triketone was readily prepared via two steps starting from commercially available, achiral 2-(n-heptyl) furan. In the final catalytic hydrogenation step, the newly introduced chiral centre directed hydrogen addition to form preferentially the desired (5Z, 8E)-diastereomer. The regio- and stereoselective amination of a single ketone moiety out of three allowed the performance of the shortest and highest yielding total synthesis of the bicyclic showcase pyrrolizidine alkaloid without the need for protecting strategies.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据