ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

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.

[img] PDF
Synthesis_of_5-p-_Hyd_roxybenzyl.pdf - Published Version
Restricted to Registered users only

Download (617Kb) | Request a copy
Official URL: http://pubs.rsc.org/en/content/articlelanding/1981...

Abstract

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
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.ernet.in/id/eprint/43319

Actions (login required)

View Item View Item