Cp* as a removable protecting group: low valent Zn(i) compounds by reductive elimination, protolytic and oxidative cleavage of Zn–Cp*

2013 ◽  
Vol 42 (29) ◽  
pp. 10540 ◽  
Author(s):  
Kerstin Freitag ◽  
Hung Banh ◽  
Chelladurai Ganesamoorthy ◽  
Christian Gemel ◽  
Rüdiger W. Seidel ◽  
...  
Keyword(s):  
Reductive Elimination ◽  
Oxidative Cleavage ◽  
Protecting Group ◽  
Low Valent

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.

Synthesis of new aromatic retinoid analogs by low-valent titanium-induced reductive elimination

1989 ◽  
Vol 54 (11) ◽  
pp. 2620-2628 ◽  
Author(s):  
Guy Solladie ◽  
Andre Girardin ◽  
Gerard Lang
Keyword(s):  
Reductive Elimination ◽  
Low Valent ◽  
Aromatic Retinoid

Reactions of sulfur containing heterocumulenes with low-valent molybdenum and tungsten complexes. Oxidative cleavage of a head-to-tail carbon disulfide dimer in a molybdenum complex

1990 ◽  
Vol 29 (25) ◽  
pp. 5074-5080 ◽  
Author(s):  
Ernesto Carmona ◽  
Agustin Galindo ◽  
Angeles Monge ◽  
Miguel Angel Munoz ◽  
Manuel L. Poveda ◽  
...  
Keyword(s):  
Carbon Disulfide ◽  
Oxidative Cleavage ◽  
Molybdenum Complex ◽  
Tungsten Complexes ◽  
Low Valent ◽  
Sulfur Containing ◽  
And Tungsten

Reductive elimination: a pathway to low-valent aluminium species

2013 ◽  
Vol 49 (28) ◽  
pp. 2858 ◽  
Author(s):  
Chelladurai Ganesamoorthy ◽  
Sinah Loerke ◽  
Christian Gemel ◽  
Paul Jerabek ◽  
Manuela Winter ◽  
...  
Keyword(s):  
Reductive Elimination ◽  
Low Valent ◽  
Aluminium Species

ChemInform Abstract: Reductive Elimination Pathways to Low-Valent Titanium Aryloxide Complexes.

ChemInform ◽  
1987 ◽  
Vol 18 (46) ◽  
Author(s):  
L. D. DURFEE ◽  
P. E. FANWICK ◽  
I. P. ROTHWELL ◽  
K. FOLTING ◽  
J. C. HUFFMAN
Keyword(s):  
Reductive Elimination ◽  
Low Valent
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