Total synthesis of (-)-deglycocadambine

Total synthesis of (-)-deglycocadambine

The first total synthesis of the monoterpene indole alkaloid (-)-deglycocadambine is achieved in 12 steps with (+)-genipin as the chiral starting material. The reported synthetic approach is characterized by an orchestrated cascade annulation between tryptamine and the highly functionalized dialdehy...

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Bibliographic Details
Main Authors: Wang, Fang-Xin, Chen, Ying-Tao, Liu, Hui, Wang, Heng-Shan, Liang, Hong, Chen, Zhen-Feng, Chi, Robin Yonggui
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Article
Language:English
Published: 2024
Subjects:
Chemistry
Dialdehydes
Oxazolidines
Online Access:https://hdl.handle.net/10356/180941
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Institution: Nanyang Technological University
Language: English
Description
Summary:The first total synthesis of the monoterpene indole alkaloid (-)-deglycocadambine is achieved in 12 steps with (+)-genipin as the chiral starting material. The reported synthetic approach is characterized by an orchestrated cascade annulation between tryptamine and the highly functionalized dialdehyde precursor, rapidly introducing the unique 6/5/6/7/6-fused pentacyclic skeleton and the ketone functional group at C19 in a convergent manner. The successful implementation of transannular oxidative cyclization at C3 for bridged oxazolidine formation in the late-stage synthetic campaign ensured the final total synthesis of this molecule.

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