Aconitine synthesis studies. A modeling construction of the functionalized BCDE tetracyclic ring system

被引：2

作者：

Guo, Tianyuan

Peng, Fuli

Song, Xueqin

Lei, Jiang

Yu, Fangzhou

Chu, Hongping

Yang, Keyang

Xu, Liang ^{[1
]}

机构：

[1] Sichuan Univ, West China Coll Pharm, Key Lab Drug Targeting, Minist Educ, R China, Chengdu 610041, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 03期

关键词：

WAGNER-MEERWEIN REARRANGEMENT; ATISANE-TYPE DITERPENOIDS; C-19-DITERPENOID ALKALOIDS; ALDER REACTION; TALATISAMINE; CHASMANINE; AMINES; CORE;

D O I：

10.1039/d2qo01740g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first model synthesis of the fully functionalized BCDE tetracyclic analogue 2 of aconitine has been accomplished. A tricyclic intermediate was prepared through highly stereospecific reduction of the ketone intermediates 14 and 16 as well as the following facile Wagner-Meerwein rearrangement. A stereoselective Michael addition and reductive cyclization involving a sequential nitrile hydration and silane promoted reduction were exploited to construct the nitrogen containing six-membered E ring bearing vicinal tertiary and quaternary centers.

引用

页码：675 / 679

页数：5

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