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Radical cyclisation based approach to lignans. Synthesis of 4-arylmethyldihydrofuran-2-ones

Srikrishna, A and Danieldoss, S (2001) Radical cyclisation based approach to lignans. Synthesis of 4-arylmethyldihydrofuran-2-ones. In: Synthetic Communications, 31 (15). pp. 2357-2364.

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Bromoacetalisation of the cinnamyl alcohols 7a-d, obtained from the corresponding benzaldehydes, generated the bromoacetals 10a-d. The 5-exo trig radical cyclisation of the bromoacetals 10a-d followed by one step hydrolysis-oxidation of the resulting cyclic acetals 11a-d furnished the title compounds 6a-d, respectively, well-established intermediates of a variety of lignans.

Item Type: Journal Article
Publication: Synthetic Communications
Publisher: Marcel Dekker
Additional Information: Copyright of this article belongs to Marcel Dekker.
Keywords: Fluoro Acid-Medium;Dibenzylbutyrolactone Lignans;Gamma-Butyrolactones;Enantioselective Synthesis;Cyclization;Neolignans;Diazoacetates;Schizandrin;Insertion;Lactones
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 08 Feb 2010 07:24
Last Modified: 08 Feb 2010 07:24
URI: http://eprints.iisc.ac.in/id/eprint/17344

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