PHOTOINDUCED MOLECULAR-TRANSFORMATIONS .153. LONG-RANGE INTRAMOLECULAR HYDROXYLATION OF C(25) OF THE CHOLESTANE SIDE-CHAIN

Authors
ORITO K SATO S SUGINOME H
Citation
K. Orito et al., PHOTOINDUCED MOLECULAR-TRANSFORMATIONS .153. LONG-RANGE INTRAMOLECULAR HYDROXYLATION OF C(25) OF THE CHOLESTANE SIDE-CHAIN, Journal of the Chemical Society. Perkin transactions. I, (1), 1995, pp. 63-67
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
1
Year of publication
1995
Pages
63 - 67
Database
ISI
SICI code
0300-922X(1995):1<63:PM.LI>2.0.ZU;2-8
Abstract
Alkoxyl radicals generated by photolysis of the hypoiodites of 5 alpha -cholestan-7 alpha-yl 4-(alpha-hydroxyphenylmethyl)phenylacetate and 5 alpha-cholestan-7 alpha-yl 3-[4-(alpha- hydroxyphenylmethyl)phenyl]pr opanoate, respectively. abstracted hydrogen from C(25) of their choles tane side chain to give novel macrocyclic-lactones. A reductive cleava ge of the benzyl ether linkage of these lactones with sodium and liqui d ammonia gave 5 alpha-cholestane-7 alpha,25-diol in good yields.