(-)-海兔内酯的全合成。

Total synthesis of (-)-kaitocephalin.

机构信息

MIRC, Department of Chemistry, KAIST, Daejeon 305-701, Korea.

出版信息

Chem Commun (Camb). 2013 Jun 7;49(45):5231-3. doi: 10.1039/c3cc42365d.

Abstract

(-)-Kaitocephalin has been synthesized. With the C9 stereocenter from Garner's aldehyde, the C4 quaternary carbon was installed by the desymmetrization of the Cbz-protected serinol. The remaining stereogenic centers were generated through mercuriocyclization, epoxidation and regioselective epoxide opening, in which the quaternary carbon most likely played crucial roles in the stereoinduction.

摘要

(-)-Kaitocephalin 已被合成。利用 Garner 醛的 C9 立体中心，通过 Cbz 保护丝氨酸的去对称化，在 C4 季碳原子上安装了季碳原子。其余的手性中心是通过汞环化、环氧化和区域选择性环氧化物开环反应生成的，其中季碳原子很可能在立体诱导中起关键作用。