DIASTEREOSELECTIVE PREPARATION OF A TRANS, TRANS 2,3-DIMETHYLCHROMAN-4-OL SKELETON - A MODEL SYNTHETIC APPROACH TO ANTI-HIV-1 ACTIVE CALOPHYLLUM COUMARINS

Authors
ISHIKAWA T OKU Y KOTAKE K
Citation
T. Ishikawa et al., DIASTEREOSELECTIVE PREPARATION OF A TRANS, TRANS 2,3-DIMETHYLCHROMAN-4-OL SKELETON - A MODEL SYNTHETIC APPROACH TO ANTI-HIV-1 ACTIVE CALOPHYLLUM COUMARINS, Tetrahedron, 53(44), 1997, pp. 14915-14928
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
44
Year of publication
1997
Pages
14915 - 14928
Database
ISI
SICI code
0040-4020(1997)53:44<14915:DPOATT>2.0.ZU;2-G
Abstract
A model synthetic study of anti-HIV-1 active Calophyllum coumarins usi ng 5, 7-dimethoxycoumarin (limettin) is described. Successive reaction s of the CsF-induced intramolecular Michael type addition of an o-tigl oylphenol followed by reduction with lithium tri-tert-butoxyaluminum h ydride led to easy and diastereoselective access to a trans, trans 2, 3-dimethylchroman-4-ol ring, which is suggested to be the most respons ible skeleton for the activity. (C) 1997 Elsevier Science Ltd.