Enantioselective total synthesis of macrolide antitumor agent (-)-lasonolide A
Enantioselective total synthesis of macrolide antitumor agent (-)-lasonolide A
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DOI：
10.1021/ol0701013
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发表时间：
2007-04-12
期刊：
影响因子：
5.2
通讯作者：
Gong, Gangli
中科院分区：
文献类型：
--
作者：
Ghosh, Arun K.;Gong, Gangli
本文报道了（-）-拉松素A的对映选择性全合成。通过分子内1，3-偶极环加成反应立体选择性地构建了四氢吡喃的上环.双环异恶唑啉导致分子中存在四氢吡喃环以及季立体中心。通过催化不对称Hetero-Diels-桤木反应组装了四氢吡喃的低级环。在该一步反应中，对映选择性地安装了三个立体中心。
An enantioselective total synthesis of (-)-lasonolide A is described. The upper tetrahydropyran ring was constructed stereoselectively by an intramolecular 1,3-dipolar cycloaddition reaction. The bicyclic isooxazoline led to the tetrahydropyran ring as well as the quaternary stereocenter present in the molecule. The lower tetrahydropyran ring was assembled by a catalytic asymmetric hetero-Diels-Alder reaction as the key step. Three stereocenters were enantioselectively installed in this single step reaction.