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Synthesis of 5-p-hydroxybenzyl-5,6-dihydro-2-naphthol, (+/-)-sequirin-d

Reddy, MP and Rao, GSK (1981) Synthesis of 5-p-hydroxybenzyl-5,6-dihydro-2-naphthol, (+/-)-sequirin-d. In: Journal of the Chemical Society-Perkin Transactions 1 (10). pp. 2662-2665.

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A high-yield six-step synthesis of sequirin D (1a), a naturally occurring norlignan, is described. Michael addition of deoxyanisoin (2) to acrylonitrile gives a ketonitrile (3), which on Wolff–Kishner reduction is reduced and hyrolysed in situ to 4,5-bis-p-methoxyphenylpentanoic acid (4). Cyclodehydration of (4) with polyphosphoric acid, followed by borohydride reduction and dehydration furnishes di-O-methylsequirin D (1b) which affords on demethylation sequirin D (1a) in an overall yield from (2) of 60%. The key synthon (4) has also been prepared by three other routes.

Item Type: Journal Article
Publication: Journal of the Chemical Society-Perkin Transactions 1
Publisher: Royal Society of Chemistry
Additional Information: Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 16 Feb 2012 06:05
Last Modified: 16 Feb 2012 06:05
URI: http://eprints.iisc.ac.in/id/eprint/43319

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