Diversity-Oriented Approach to Biologically Relevant Molecular Frameworks Starting with β-Naphthol and Using the Claisen Rearrangement and Olefin Metathesis as Key Steps

2006 ◽  
Vol 12 (31) ◽  
pp. 8024-8038 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Kalyaneswar Mandal ◽  
Arti Tiwari ◽  
Shaikh M. Mobin
Keyword(s):  
Olefin Metathesis ◽  
Claisen Rearrangement ◽  
Biologically Relevant ◽  
Key Steps ◽  
Oriented Approach

Copper-catalyzed alkynylation/annulation cascades of N-allyl ynamides: regioselective access to medium-sized N-heterocycles

2021 ◽  
Vol 8 (1) ◽  
pp. 18-24
Author(s):  
Xu-Heng Yang ◽  
Jian Huang ◽  
Fang Wang ◽  
Zhuoliang Liu ◽  
Yujiao Li ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Synthetic Strategy ◽  
Key Steps

A synthetic strategy based on sequential application of aza-Claisen rearrangement, C–H functionalization, C–N coupling and cyclization as key steps has been developed for the synthesis of 6-, 7-, 8-, and 9-membered rings N-heterocycles.

scholarly journals Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins

2018 ◽  
Vol 14 ◽  
pp. 2991-2998 ◽  
Author(s):  
Christiane Schultze ◽  
Bernd Schmidt
Keyword(s):  
Double Bond ◽  
Olefin Metathesis ◽  
Claisen Rearrangement ◽  
Allylic Oxidation ◽  
Allyl Ether ◽  
Ring Closing Metathesis ◽  
Wittig Olefination

8-Allylcoumarins are conveniently accessible through a microwave-promoted tandem Claisen rearrangement/Wittig olefination/cyclization sequence. They serve as a versatile platform for the annellation of five- to seven-membered rings using ring-closing olefin metathesis (RCM). Furano-, pyrano-, oxepino- and azepinocoumarins were synthesized from the same set of precursors using Ru-catalyzed double bond isomerizations and RCM in a defined order. One class of products, pyrano[2,3-f]chromene-2,8-diones, were inaccessible through direct RCM of an acrylate, but became available from the analogous allyl ether via an assisted tandem catalytic RCM/allylic oxidation sequence.

Ring-Closing Metathesis Approach to Cage Propellanes Containing Oxepane and Tetrahydrofuran Hybrid System

Synthesis ◽  
2017 ◽  
Vol 49 (24) ◽  
pp. 5339-5350 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Subba Cheekatla ◽  
Darshan Mhatre
Keyword(s):  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ring Closing Metathesis ◽  
Cage Compounds ◽  
Transannular Cyclization ◽  
Diels Alder Reaction ◽  
Grignard Addition ◽  
Key Steps ◽  
First Time

The preparation of a variety of structurally interesting oxygenated cage compounds involving atom-economic processes such as Claisen rearrangement, Diels–Alder reaction, [2+2] photocycloaddition, and ring-closing metathesis (RCM) as key steps is reported. For the first time, oxepane ring system is introduced in cage framework using olefin metathesis as a key step. These cage systems assembled here are difficult to prepare by traditional methods. The synthetic sequence described here opens up new routes to higher order polycycles containing heteroatoms without the involvement of protecting groups. Transannular cyclization observed during Grignard addition and the RCM protocol used here may be applicable to generate unknown oxygenated cage systems.

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