Iodomesitylene-Catalyzed Oxidative Cleavage of Carbon−Carbon Double and Triple Bonds Usingm-Chloroperbenzoic Acid as a Terminal Oxidant

2009 ◽  
Vol 131 (4) ◽  
pp. 1382-1383 ◽  
Author(s):  
Kazunori Miyamoto ◽  
Yoshihisa Sei ◽  
Kentaro Yamaguchi ◽  
Masahito Ochiai
Keyword(s):  
Oxidative Cleavage ◽  
Triple Bonds

ChemInform Abstract: PIFA-Mediated Esterification Reaction of Alkynes with Alcohols via Oxidative Cleavage of Carbon Triple Bonds.

ChemInform ◽  
2014 ◽  
Vol 45 (36) ◽  
pp. no-no
Author(s):  
Qing Jiang ◽  
An Zhao ◽  
Bin Xu ◽  
Jing Jia ◽  
Xin Liu ◽  
...  
Keyword(s):  
Oxidative Cleavage ◽  
Esterification Reaction ◽  
Triple Bonds

PIFA-Mediated Esterification Reaction of Alkynes with Alcohols via Oxidative Cleavage of Carbon Triple Bonds

2014 ◽  
Vol 79 (6) ◽  
pp. 2709-2715 ◽  
Author(s):  
Qing Jiang ◽  
An Zhao ◽  
Bin Xu ◽  
Jing Jia ◽  
Xin Liu ◽  
...  
Keyword(s):  
Oxidative Cleavage ◽  
Esterification Reaction ◽  
Triple Bonds

Synthesis of (15E)-17β-hydroxy-5α-androstane-3,15-dione 15-[O-(Carboxymethyl)]oxime, New Hapten for Dihydrotestosterone (17β-hydroxy-5α-androstan-3-one)

1997 ◽  
Vol 62 (10) ◽  
pp. 1642-1649 ◽  
Author(s):  
Ivan Černý ◽  
Tereza Slavíková ◽  
Vladimír Pouzar
Keyword(s):  
Hydroxy Group ◽  
Carboxy Group ◽  
Title Compound ◽  
Oxidative Cleavage ◽  
Hydroxy Derivative ◽  
Borohydride Reduction ◽  
Protecting Group ◽  
Free Hydroxy Group

Addition of 4-methoxybenzyl alcohol to 3β-hydroxy-5α-androst-15-en-17-one gave the mixture of isomeric 15-(4-methoxyphenyl)methoxy derivatives from which, after acetylation and chromatography, the major 15β isomer was separated. Borohydride reduction gave 17β-hydroxy derivative which was protected as methoxymethyl ether. Oxidative cleavage of protecting group at position 15 and the subsequent Jones oxidation afforded corresponding 15-ketone. Its oximation with O-(carboxymethyl)hydroxylamine, deacetylation and methylation with diazomethane gave protected O-(carboxymethyl)oxime derivative with free hydroxy group at position 3. Its oxidation afforded dihydrotestosterone derivative and successive deprotection of position 17 and of carboxy group led to final (15E)-17β-hydroxy-5α-androstane-3,15-dione 15-[O-(carboxymethyl)]oxime. The title compound was designed as dihydrotestosterone hapten for heterologous radioimmunoassays.

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