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.
Synthesis_of_5-p-_Hyd_roxybenzyl.pdf - Published Version
Restricted to Registered users only
Download (617Kb) | Request a copy
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|
Actions (login required)