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

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 Roche convergent Wittig-Horner approach. The key steps in the preparation of...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 65; no. 21; pp. 6978 - 6983
Main Authors Fernandez-Gacio, A, Vitale, C, Mourino, A
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 20.10.2000
Subjects
Animals
Binding, Competitive
Calcitriol - analogs & derivatives
Calcitriol - chemical synthesis
Calcitriol - metabolism
Cattle
Chemistry
Chemistry, Organic
In Vitro Techniques
Molecular Conformation
Physical Sciences
Receptors, Calcitriol - metabolism
Science & Technology
Thymus Gland - metabolism
BREAST-CANCER
D METABOLITES
PHOSPHONATES
VITAMIN-D ANALOGS
RING
MICE
D CALCIFEROL
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Summary: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 Roche 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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo000579j