Stereoselective Total Synthesis of Hetisine‐type C 20 ‐Diterpenoid Alkaloids: Spirasine IV and XI | Zendy

Zhang Quanzheng | Zendy; Zhang Zhongshan | Zendy; Huang Zhong | Zendy; Zhang Changhui | Zendy; Xi Song | Zendy; Zhang Min | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

Stereoselective Total Synthesis of Hetisine‐type C 20 ‐Diterpenoid Alkaloids: Spirasine IV and XI

Author(s) -

Zhang Quanzheng,

Zhang Zhongshan,

Huang Zhong,

Zhang Changhui,

Xi Song,

Zhang Min

Publication year - 2018

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201711414

Subject(s) - intramolecular force , stereoselectivity , moiety , chemistry , regioselectivity , aldol reaction , stereochemistry , cycloaddition , bicyclic molecule , ring (chemistry) , octane , total synthesis , terpenoid , organic chemistry , catalysis

The first total synthesis of the architecturally complex hetisine‐type heptacyclic C 20 ‐diterpenoid alkaloids (±)‐spirasine IV and XI is reported. The A/F/G/C tetracyclic skeleton with the challenging N−C6 and C14−C20 linkages was efficiently constructed by an intramolecular azomethine‐ylide‐based 1,3‐dipolar cycloaddition with unusual regioselectivity. SmI 2 ‐mediated free‐radical addition to the arene moiety without prior dearomatization and a stereoselective intramolecular aldol reaction further enabled rapid access to the hetisine core, providing a bicyclo[2.2.2]octane ring with a new oxygen substitution pattern.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research