不对称全合成石松生物碱五环：石杉碱-Q。
Asymmetric total synthesis of a pentacyclic Lycopodium alkaloid: huperzine-Q.
机构信息
Graduate School of Pharmaceutical Sciences, Chiba University, Yayoi-cho, Inage-ku, Chiba, Japan.
出版信息
Angew Chem Int Ed Engl. 2011 Aug 22;50(35):8025-8. doi: 10.1002/anie.201103550. Epub 2011 Jul 12.
PMID:21751323
Abstract
Right on Q: the first asymmetric total synthesis of (-)-huperzine-Q, which possesses six stereogenic centers and a spiroaminal moiety, has been achieved in 19 steps and 16.4 % overall yield. This synthesis involved a novel stereoselective Pauson-Khand reaction, a vinyl Claisen rearrangement, and a biomimetic spiroaminal formation. TBDPS=tert-butyldiphenylsilyl.
摘要
右对 Q：(-)-石杉碱-Q 的首次不对称全合成，其具有六个手性中心和一个螺环亚胺部分，已在 19 步和 16.4%的总收率下实现。该合成涉及新颖的立体选择性 Pauson-Khand 反应、乙烯基 Claisen 重排和仿生螺环亚胺形成。TBDPS=叔丁基二苯基硅基。
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