SYNTHESIS OF A CONFORMATIONALLY RESTRAINED 4-ARYL-THIOPHENE-3-HEPTENOIC ACID AND ITS EVALUATION AS AN HMG COENZYME-A REDUCTASE INHIBITOR

Authors
COPPOLA GM DAMON RE ENGSTROM RG
Citation
Gm. Coppola et al., SYNTHESIS OF A CONFORMATIONALLY RESTRAINED 4-ARYL-THIOPHENE-3-HEPTENOIC ACID AND ITS EVALUATION AS AN HMG COENZYME-A REDUCTASE INHIBITOR, Heterocyclic communications, 4(2), 1998, pp. 105-111
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocyclic communications → ACNP
ISSN journal
07930283
Volume
4
Issue
2
Year of publication
1998
Pages
105 - 111
Database
ISI
SICI code
0793-0283(1998)4:2<105:SOACR4>2.0.ZU;2-M
Abstract
A 4-phenylthiophene tethered to the 5-position of the heterocycle was synthesized from 1-benzosuberone. The key steps in the synthesis were the tandem thiolacetate hydrolysis - Michael addition intramolecular W ittig reaction ((5) under bar --> (7) under bar) and the chelation-con trolled reduction of the hydroxy beta-ketoester (<(12)under bar> --> < (13)under bar>). The product <(14)under bar> exhibited nearly identica l in vivo potency to the non-tethered analogs.