A REVISITATION OF THE CLEMMENSEN REDUCTION OF DIOSGENIN - CHARACTERIZATION OF BY-PRODUCTS AND THEIR USE IN THE PREPARATION OF (25R)-26-HYDROXYSTEROLS

Authors
NI Y KIM HS WILSON WK KISIC A SCHROEPFER GJ
Citation
Y. Ni et al., A REVISITATION OF THE CLEMMENSEN REDUCTION OF DIOSGENIN - CHARACTERIZATION OF BY-PRODUCTS AND THEIR USE IN THE PREPARATION OF (25R)-26-HYDROXYSTEROLS, Tetrahedron letters, 34(23), 1993, pp. 3687-3690
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
23
Year of publication
1993
Pages
3687 - 3690
Database
ISI
SICI code
0040-4039(1993)34:23<3687:AROTCR>2.0.ZU;2-P
Abstract
Four major byproducts of the Clemmensen reduction of diosgenin have be en isolated and identified: -18-nor-17alpha-cholesta-5,13-diene-3beta, 26-diol, dihydrodiosgenin, 2E,25R)-cholesta-5,22-diene-3beta,16beta,26 -triol, and its 22Z isomer. These byproducts were used to prepare deut erium- and tritium-labeled (25R)-26-hydroxycholesterol (3) and DELTA22 analogs of 3.