A NOVEL AND PRACTICAL ROUTE TO A-RING ENYNE SYNTHON FOR 1-ALPHA,25-DIHYDROXYVITAMIN D-3 ANALOGS - SYNTHESIS OF A-RING DIASTEREOMERS OF 1-ALPHA,25-DIHYDROXYVITAMIN D-3 AND 2-METHYL-1,25-DIHYDROXYVITAMIN D-3

Authors
KONNO K MAKI S FUJISHIMA T LIU ZP MIURA D CHOKKI M TAKAYAMA H
Citation
K. Konno et al., A NOVEL AND PRACTICAL ROUTE TO A-RING ENYNE SYNTHON FOR 1-ALPHA,25-DIHYDROXYVITAMIN D-3 ANALOGS - SYNTHESIS OF A-RING DIASTEREOMERS OF 1-ALPHA,25-DIHYDROXYVITAMIN D-3 AND 2-METHYL-1,25-DIHYDROXYVITAMIN D-3, Bioorganic & medicinal chemistry letters, 8(2), 1998, pp. 151-156
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
8
Issue
2
Year of publication
1998
Pages
151 - 156
Database
ISI
SICI code
0960-894X(1998)8:2<151:ANAPRT>2.0.ZU;2-V
Abstract
A novel and practical route to the A-ring enyne synthon (2), which can be versatile for a variety of A-ring analogs of 1 alpha,25-dihydroxyv itamin D-3 (1), was developed. This novel method led to an improved sy nthesis of the A-ring diastereomers of 1, the compounds 13-15, and syn thesis of the new analogs, 2-methyl-1,25-dihydroxyvitamin D-3 (4) with its all possible diastereomers. The biological evaluation of the 2-me thyl analogs showed the alpha alpha beta-isomer to be more potent than 1. (C) 1998 Elsevier Science Ltd. All rights reserved.