Synthesis of new aromatic (C17-C20)-locked side-chain analogues of calcitriol (1 alpha,25-dihydroxyvitamin D-3)

Authors
Fernandez-Gacio, A Vitale, C Mourino, A
Citation
A. Fernandez-gacio et al., Synthesis of new aromatic (C17-C20)-locked side-chain analogues of calcitriol (1 alpha,25-dihydroxyvitamin D-3), J ORG CHEM, 65(21), 2000, pp. 6978-6983
Citations number
40
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
21
Year of publication
2000
Pages
6978 - 6983
Database
ISI
SICI code
0022-3263(20001020)65:21<6978:SONA(S>2.0.ZU;2-V
Abstract
The synthesis of four new analogues of calcitriol (1 alpha ,25-(OH)(2)-D-3) possessing aromatic and conjugated double bond units at the side chain are described. The triene system is introduced using the Lythgoe-Hoffmann La R oche convergent Wittig-Horner approach. The key steps in the preparation of the requisite upper fragments are the introduction of the side chain with the E-conjugated aromatic system and its photochemical conversion to the Z counterpart.