Type II Intramolecular [5+2] Cycloaddition: Facile Synthesis of Highly Functionalized Bridged Ring Systems

被引：77

作者：

Mei, Guangjian ^{[2
]}

Liu, Xin ^{[1
]}

Qiao, Chuang ^{[2
]}

Chen, Wei ^{[2
]}

Li, Chuang-chuang ^{[1
,2
]}

机构：

[1] South Univ Sci & Technol China, Dept Chem, Shenzhen 518055, Peoples R China

[2] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 06期

关键词：

bridged ring systems; cycloaddition; diastereoselectivity; endo selectivity; natural products; DIELS-ALDER REACTION; TUMOR PROMOTERS; CYCLO-ADDITIONS; VINYLCYCLOPROPANES; METAL; 1ST; CYCLOISOMERIZATION; WELWITINDOLINONES; CYCLOCITRINOL; ALKALOIDS;

D O I：

10.1002/anie.201410806

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A typeII intramolecular oxidopyrylium-mediated [5+2] cycloaddition reaction allows the efficient and diastereoselective formation of various highly functionalized and synthetically challenging bridged seven-membered ring systems (such as bicyclo[4.4.1]undecane, bicyclo[4.3.1]decane, bicyclo[5.4.1]dodecane, and bicyclo[6.4.1]]tridecane). This simple, thermal, direct transformation has a broad substrate scope and is high yielding, with high functional-group tolerance and unique endo selectivity. The highly strained tricyclic cores of ingenol mebutate (picato) and cyclocitrinol are synthesized efficiently and diastereoselectively using this methodology.

引用

页码：1754 / 1758

页数：5

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