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

Pedireddi, N and G, Satyanarayana (2016) One-pot C–C/C–O bond formation: synthesis of spirocyclic lactones. RSC Advances (6). pp. 837-843. ISSN 2046-2069

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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 (FeCl3) 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.

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IITH Creators:
IITH CreatorsORCiD
G, SatyanarayanaUNSPECIFIED
Item Type: Article
Subjects: Chemistry > Organic chemistry
Divisions: Department of Chemistry
Depositing User: Team Library
Date Deposited: 21 Jan 2016 05:19
Last Modified: 21 Jan 2016 05:19
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