Synthesis of Polycyclic Frameworks through Iron-Catalyzed Intramolecular [5+2] Cycloaddition

被引：10

作者：

Liu, Yongjiang ^{[1
]}

Zhang, Yanhui ^{[1
]}

Wang, Xiao ^{[1
]}

Fu, Shaomin ^{[1
]}

Liu, Bo ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China

来源：

SYNLETT | 2018年 / 29卷 / 15期

关键词：

C-8/C-19-diterpenoid alkaloids; phomopsterone B; Iron-catalyzed; 5+2] cycloaddition; C-19-DITERPENOID ALKALOIDS; DITERPENOID ALKALOIDS; C-20-DITERPENOID ALKALOIDS; RADICAL CYCLIZATION; TALATISAMINE; CONSTRUCTION; PACTAMYCIN; HETIDINE; SYSTEMS;

D O I：

10.1055/s-0037-1610258

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and efficient approach to the core of the C (18) /C (19) diterpenoid alkaloids and phomopsterone B is reported. Both syntheses share the same iron-catalyzed intramolecular [5+2] cycloaddition to assemble the tricyclo[6.3.1.0 (1,6]) ]dodecane skeleton. The following approach to the 6/5/6/7 tetracyclic core scaffold of C (18) /C (19) diterpenoid alkaloids features a regioselective Grignard addition/thermal Claisen rearrangement/RCM cyclization. Meanwhile the synthetic steps to access the spiro 6/5/6 tricyclic subunits of phomopsterone B were characterized as intramolecular aldol reaction, Wacker oxidation, and Criegee reaction.

引用

页码：1978 / 1982

页数：5

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