One-pot C-C/C-O bond formation: synthesis of spirocyclic lactones

An efficient and practical method for the synthesis of novel spiro(tri or tetra)cyclic lactones via the formation of C-C and C-O bonds in one-pot is presented. The method was successful under Lewis acidic (FeCl 3 ) conditions and enabled the formation of spiro(tri or tetra)cyclic lactones from simpl...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2016-01, Vol.6 (2), p.837-843
Main Authors: Niharika, Pedireddi, Satyanarayana, Gedu
Format: Article
Language:English
Subjects:
Biological properties
Bonding
Carbon-carbon composites
Coupling
Esters
Formations
Lactones
Synthesis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An efficient and practical method for the synthesis of novel spiro(tri or tetra)cyclic lactones via the formation of C-C and C-O bonds in one-pot is presented. The method was successful under Lewis acidic (FeCl 3 ) conditions and enabled the formation of spiro(tri or tetra)cyclic lactones from simple aliphatic exocyclic enoate esters as reacting partners with phenols. Remarkably, the usual self-aromatization of cyclohexanone based enoate esters, under such Lewis acidic conditions is overridden by intermolecular coupling. Significantly, the method was amenable to indanone derived esters as well and furnished novel spiro(tetra or penta)cyclic lactones bearing simple to dense functionalities on the aromatic rings. Notably, these novel spirocyclic systems constitute core structures of natural/unnatural compounds that show good biological properties. An efficient and practical method for the synthesis of novel spiro(tri or tetra)cyclic lactones via the formation of C-C and C-O bonds in one-pot is presented.
ISSN:2046-2069
2046-2069
DOI:10.1039/c5ra22684h