Lewis acid promoted C–C and copper-catalyzed C–O bond formation: synthesis of neoflavans†

B, Suchand and J, Krishna and K, Mritunjoy and G, Satyanarayana (2014) Lewis acid promoted C–C and copper-catalyzed C–O bond formation: synthesis of neoflavans†. RSC Advances, 4. pp. 13941-13945. ISSN 2046-2069

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Abstract

An intramolecular [Cu]-catalyzed C–O bond formation for the synthesis of neoflavans is presented. Lewis acid promoted Friedel– Crafts Michael addition of electron rich aromatic systems onto the double bond of the cinnamate esterwas employed to furnish a b-diaryl ester. Electrophilic aromatic bromination of the b-diaryl ester and reduction/Grignard addition furnished the required precursor alcohols. The method is applicable to the synthesis of neoflavans containing tertiary as well as quaternary carbon centers. Significantly, the neoflavan substructures are present in biologically active compounds.

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IITH Creators:
IITH CreatorsORCiD
G, SatyanarayanaUNSPECIFIED
Item Type: Article
Subjects: ?? sub5.8 ??
Divisions: Department of Chemistry
Depositing User: Mr. Siva Shankar K
Date Deposited: 30 Sep 2014 06:57
Last Modified: 24 Sep 2015 10:22
URI: http://raiith.iith.ac.in/id/eprint/158
Publisher URL: http://dx.doi.org/10.1039/c4ra00048j
OA policy: http://www.sherpa.ac.uk/romeo/issn/2046-2069/
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