Synthesis of Angular Triquinane and [4.3.3]Propellane Derivatives via Ring-Rearrangement Olefin Metathesis

被引：0

作者：

Kotha, Sambasivarao ^{[1
]}

Agrawal, Arpit ^{[1
]}

Ansari, Saima ^{[1
]}

机构：

[1] Indian Inst Informat Technol, Dept Chem, Mumbai 400076, Maharashtra, India

来源：

CHEMISTRYSELECT | 2021年 / 6卷 / 41期

关键词：

Allylation; Angular triquinane; Cyclopentanoid; Metathesis; Polycyclic; Propellane; CROSS-ENYNE METATHESIS; ENANTIOSELECTIVE SYNTHESIS; CLOSING METATHESIS; NATURAL-PRODUCTS; GENERAL-APPROACH; WEISS REACTION; NORBORNENE; COMPLEXES; ACCESS; CORE;

D O I：

10.1002/slct.202103226

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, a simple and useful approach to angular triquinane and [4.3.3]propellane moieties is described via olefin metathesis starting from exo and endo Diels-Alder (DA) adducts containing norbornene unit. This approach involves DA reaction, and ring-rearrangement metathesis (RRM) as key steps. Strained norbornene derivatives on allylation at bridgehead position(s) followed by ring-opening metathesis and ring-closing metathesis sequence delivered angular triquinane and also stereochemically different propellane derivatives.

引用

页码：11178 / 11181

页数：4

共 50 条

[1] Design and synthesis of propellane derivatives and oxa-bowls via ring-rearrangement metathesis as a key step
Kotha, Sambasivarao
Gunta, Rama
[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1727 - 1731
[2] Design and synthesis of oxacycles from norbornene derivatives via ring-opening metathesis and ring-rearrangement metathesis
Kotha, Sambasivarao
Ravikumar, Ongolu
Sreevani, Gaddamedi
[J]. TETRAHEDRON, 2016, 72 (42) : 6611 - 6615
[3] Ring-rearrangement metathesis
Holub, Nicole
Blechert, Siegfried
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (09) : 1064 - 1082
[4] Ring-Rearrangement Metathesis of Cyclopropenes: Synthesis of Heterocycles
Miege, Frederic
Meyer, Christophe
Cossy, Janine
[J]. ORGANIC LETTERS, 2010, 12 (02) : 248 - 251
[5] Ring-rearrangement metathesis of bicyclic amino acid derivatives
Maechling, S
Norman, SE
McKendrick, JE
Basra, S
Köppner, K
Blechert, S
[J]. TETRAHEDRON LETTERS, 2006, 47 (02) : 189 - 192
[6] Synthesis of fused azacycle via Overman rearrangement and ring-rearrangement metathesis as key steps
Kotha, Sambasivarao
Ravikumar, Ongolu
[J]. TETRAHEDRON LETTERS, 2016, 57 (18) : 1994 - 1996
[7] Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps
Kotha, Sambasivarao
Ravikumar, Ongolu
Majhi, Jadab
[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1503 - 1508
[8] Diastereoselective ring-rearrangement metathesis
Böhrsch, V
Neidhöfer, J
Blechert, S
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) : 1302 - 1305
[9] Recent applications of ring-rearrangement metathesis in organic synthesis
Kotha, Sambasivarao
Meshram, Milind
Khedkar, Priti
Banerjee, Shaibal
Deodhar, Deepak
[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1833 - 1864
[10] Synthesis of Intricate Fused N-Heterocycles via Ring-Rearrangement Metathesis
Kotha, Sambasivarao
Gunta, Rama
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (16): : 8527 - 8535

← 1 2 3 4 5 →