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

共 50 条

[31] Iron-Catalyzed Intramolecular Perezone-Type [5+2] Cycloaddition: Access to Tricyclo[6.3.1.01,6]dodecane
Liu, Yongjiang
Wang, Xiao
Chen, Song
Fu, Shaomin
Liu, Bo
[J]. ORGANIC LETTERS, 2018, 20 (10) : 2934 - 2938
[32] Asymmetric total synthesis of (+)-aphanamol I via a Rh(I)-catalyzed intramolecular [5+2] allenyl vinylcyclopropane cycloaddition.
Wender, PA
Zhang, L
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U196 - U197
[33] RhI-Catalyzed Two-Component [(5+2)+1] Cycloaddition Approach toward [5-8-5] Ring Systems
Huang, Feng
Yao, Zhong-Ke
Wang, Yi
Wang, Yuanyuan
Zhang, Jialing
Yu, Zhi-Xiang
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) : 1555 - 1559
[34] Cationic [5+2] cycloaddition reactions promoted by trimethylsilyl triflate in highly polar media
Collins, JL
Grieco, PA
Walker, JK
[J]. TETRAHEDRON LETTERS, 1997, 38 (08) : 1321 - 1324
[35] SYNTHESIS OF POLYCYCLIC RING-SYSTEMS VIA INTRAMOLECULAR [2+2]-CYCLOADDITION REACTIONS OF CYCLOPROPENE DERIVATIVES
PADWA, A
RIEKER, W
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1980, 180 (AUG): : 142 - ORGN
[36] SYNTHESIS OF POLYCYCLIC RING-SYSTEMS VIA INTRAMOLECULAR [2+2]-CYCLOADDITION REACTIONS OF CYCLOPROPENE DERIVATIVES
PADWA, A
BLACKLOCK, TJ
RIEKER, WF
[J]. ISRAEL JOURNAL OF CHEMISTRY, 1981, 21 (2-3) : 157 - 163
[37] Atom-Economic Synthesis of Highly Functionalized Bridged Ring Systems Initiated by Ring Expansion of Indene-1,3-dione
Mu, Yuanyang
Yao, Qiyi
Yin, Liqiang
Fu, Siyi
Wang, Mengdan
Yuan, Yang
Kong, Lingkai
Li, Yanzhong
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (09): : 6755 - 6764
[38] A facile synthesis of 2-methyl-1,4-benzodiazepin-5-ones via intramolecular azide cycloaddition
Broggini, G
Zecchi, G
Molteni, G
[J]. GAZZETTA CHIMICA ITALIANA, 1997, 127 (12): : 809 - 810
[39] Intramolecular cationic [5+2]cycloaddition reaction of penta-substituted phenols by using anodic oxidation
Takakura, H
Yamamura, S
[J]. TETRAHEDRON LETTERS, 1998, 39 (22) : 3717 - 3720
[40] Preparation and Diels-Alder cycloaddition of 2-acyloxyacroleins. Facile synthesis of functionalized taxol A-ring synthons
Funk, RL
Yost, KJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08): : 2598 - 2599

← 1 2 3 4 5 →