Total synthesis of 25-hydroxy-16,23E-diene vitamin D-3 and 1 alpha,25-dihydroxy-16,23E-diene vitamin D-3: Separation of genomic and nongenomic vitamin D activities

Authors
Kabat, MM Burger, W Guggino, S Hennessy, B Iacobelli, JA Takeuchi, K Uskokovic, MR
Citation
Mm. Kabat et al., Total synthesis of 25-hydroxy-16,23E-diene vitamin D-3 and 1 alpha,25-dihydroxy-16,23E-diene vitamin D-3: Separation of genomic and nongenomic vitamin D activities, BIO MED CH, 6(11), 1998, pp. 2051-2059
Citations number
32
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY
ISSN journal
09680896 → ACNP
Volume
6
Issue
11
Year of publication
1998
Pages
2051 - 2059
Database
ISI
SICI code
0968-0896(199811)6:11<2051:TSO2VD>2.0.ZU;2-G
Abstract
Separation of genomic and nongenomic vitamin D activities was achieved by s tructural modification of 1,25-dihydroxy vitamin D-3 by introduction of 16 and 23E double bonds. The modified compound 3, lacking a 1 alpha-hydroxy gr oup, exhibits only nongenomic activity. Its 1 alpha-hydroxy relative 4 expr esses fully both genomic and nongenomic activities. A. total synthesis of a nalogues 3 and 4 is described. (C) 1998 Elsevier Science Ltd. All rights re served.