SYNTHESIS OF (25R)-CHOLEST-5-ENE-3-BETA,26-DIOL AND ITS RADIOLABELED ANALOG

Authors
DAMBRA TE JAVITT NB NAKANISHI K WARCHOL T
Citation
Te. Dambra et al., SYNTHESIS OF (25R)-CHOLEST-5-ENE-3-BETA,26-DIOL AND ITS RADIOLABELED ANALOG, Tetrahedron letters, 38(22), 1997, pp. 3801-3804
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
22
Year of publication
1997
Pages
3801 - 3804
Database
ISI
SICI code
0040-4039(1997)38:22<3801:SO(AIR>2.0.ZU;2-X
Abstract
A new, convenient and stereoselective route to the synthesis of (25R)- cholest-5-ene-3 beta,26-diol (1) and its radiolabeled analog 4 is desc ribed. The key step is a Julia condensation of sulfone 6 with aldehyde 12 to furnish compound 13. Further reduction of the alpha-hydroxysulf one moiety afforded 22,23-unsaturated i-steroid 14. The double bond wa s reduced by hydrogen and by tritium to provide substrates for the pre paration of 1 and 4, respectively. (C) 1997 Elsevier Science Ltd.