Oxo reduction

We have found recently that S. iividaTis TK24 (the most widely used host for cloning of anthracycline biosynthesis genes and one of the major cloning strains used in Strepto-myces research), as well as Strepromyces sp. strain C5, Srreptomyces cocfcolor A3(2), and S. peucen us ATCC 29050 all carry out the 13-oxo reduction of doxorubicin, daunorubicin, carminomycin, and idarubicin (as well as their lycones) to the respective 13-hydroxy species (244 Dickens ML and ohl WR, unpublished data). It is presumed at this time that perhaps multiple emymes can carry out this reduction. 

Cobalt has an odd number of electrons, and does not form a simple carbonyl in oxidation state 0. However, carbonyls of formulae Co2(CO)g, Co4(CO)i2 and CoJCO),6 are known reduction of these by an alkali metal dissolved in liquid ammonia (p. 126) gives the ion [Co(CO)4] ". Both Co2(CO)g and [Co(CO)4]" are important as catalysts for organic syntheses. In the so-called oxo reaction, where an alkene reacts with carbon monoxide and hydrogen, under pressure, to give an aldehyde, dicobalt octacarbonyl is used as catalyst ... 

Ethynodiol diacetate (53) is prepared by reduction of the 3-oxo group of norethindrone (28) with lithium tributoxyalurninum hydride, followed by acylation with acetic anhydride-pyridine (78,79). It has been reported that higher yields can be obtained in the reduction step by using triethylanainoalurninum hydride (80). 

Lynestrenol is the des-3-oxo derivative of norethindrone (28). It has been prepared through a similar synthetic pathway as aHylestrenol (37) (52), ie, addition of potassium acetyUde, rather than aHyl magnesium bromide, affords lynestrenol (73). Lynestrenol is also available from norethindrone (28). Reduction of the 3-keto group is accompHshed by treating norethindrone (28) with sodium borohydride in the presence of trifluoro- or trichloroacetic acid... 

Oxo aldehyde products range from C to C, ie, detergent range, and are employed principally as intermediates to alcohols, acids, polyols, and esters formed by the appropriate reduction, oxidation, or condensation chemistry. The 0x0 reaction has been the subject of various reviews (4). 

The cake produced by the digestion is extracted with cold water and possibly with some diluted acids from the subsequent processes. During the cake dissolution it is necessary to maintain the temperature close to 65°C, the temperature of iron sulfate maximum solubiUty. To prevent the reoxidation of the Fe " ions during processing, a small amount of Ti " is prepared in the system by the Ti reduction. The titanium extract, a solution of titanium oxo-sulfate, iron sulfate, and sulfuric acid, is filtered off. Coagulation agents are usually added to the extract to faciUtate the separation of insoluble sludge. 

Carbazole, 2-hydroxy-reactions with citral, 4, 235 Carbazole, 2-hydroxy-9-methyl-synthesis, 4, 294 Carbazole, N-hydroxymethyl-as metabolite of carbazole, 1, 230 Carbazole, N-isopropyl-PE spectroscopy, 4, 190 Carbazole, A7-methyl- N NMR, 4, 175 X-ray spectroscopy, 4, 163 Carbazole, 1-nitro-synthesis, 4, 282 Carbazole, tetrahydro-dehydrogenation, 4, 282, 312 synthesis, 4, 107, 337, 353 Carbazole, 1,2,3,4-tetrahydro-reduction, 4, 255, 256 synthesis, 4, 312, 325, 352 Carbazole, 1,2,3,4-tetrahydro-1 -oxo-synthesis, 4, 337 Carbazole, 9-trifluoroacetyl-synthesis, 4, 218 Carbazole, vinyl-polymers, 1, 275, 301 Carbazole, 9-vinyl-copolymer... 

Pteridine, 6-oxo-5,6,7,8-tetrahydro-electrochemistry, 3, 285 Pteridine, 7-oxo-5,6,7,8-tetrahydro-electrochemistry, 3, 285 Pteridine, 2-phenyl-structure, 3, 266 Pteridine, 4-phenyl-structure, 3, 266 Pteridine, 7-phenyl-oxidation, 3, 305 Pteridine, 2,4,6,7-tetraamino-synthesis, 3, 291 Pteridine, 2,4,6,7-tetrabromo-reactions, 3, 291 Pteridine, 2,4,6,7-tetrachloro-hydrolysis, 3, 291 properties, 3, 267 Pteridine, 1,2,3,4-tetrahydro-structure, 3, 280 Pteridine, 5,6,7,8-tetrahydro-reduction, 3, 280 synthesis, 3, 305 Pteridine, 2,4,6,7-tetramethyl-NMR, 3, 266... 

Purines, N-alkyl-N-phenyl-synthesis, 5, 576 Purines, alkylthio-hydrolysis, 5, 560 Mannich reaction, 5, 536 Michael addition reactions, 5, 536 Purines, S-alkylthio-hydrolysis, 5, 560 Purines, amino-alkylation, 5, 530, 551 IR spectra, 5, 518 reactions, 5, 551-553 with diazonium ions, 5, 538 reduction, 5, 541 UV spectra, 5, 517 Purines, N-amino-synthesis, 5, 595 Purines, aminohydroxy-hydrogenation, 5, 555 reactions, 5, 555 Purines, aminooxo-reactions, 5, 557 thiation, 5, 557 Purines, bromo-synthesis, 5, 557 Purines, chloro-synthesis, 5, 573 Purines, cyano-reactions, 5, 550 Purines, dialkoxy-rearrangement, 5, 558 Purines, diazoreactions, 5, 96 Purines, dioxo-alkylation, 5, 532 Purines, N-glycosyl-, 5, 536 Purines, halo-N-alkylation, 5, 529 hydrogenolysis, 5, 562 reactions, 5, 561-562, 564 with alkoxides, 5, 563 synthesis, 5, 556 Purines, hydrazino-reactions, 5, 553 Purines, hydroxyamino-reactions, 5, 556 Purines, 8-lithiotrimethylsilyl-nucleosides alkylation, 5, 537 Purines, N-methyl-magnetic circular dichroism, 5, 523 Purines, methylthio-bromination, 5, 559 Purines, nitro-reactions, 5, 550, 551 Purines, oxo-alkylation, 5, 532 amination, 5, 557 dipole moments, 5, 522 H NMR, 5, 512 pJfa, 5, 524 reactions, 5, 556-557 with diazonium ions, 5, 538 reduction, 5, 541 thiation, 5, 557 Purines, oxohydro-IR spectra, 5, 518 Purines, selenoxo-synthesis, 5, 597 Purines, thio-acylation, 5, 559 alkylation, 5, 559 Purines, thioxo-acetylation, 5, 559... 

In substitutive nomenclature the use of the prefix oxo- or the suffix -one means the insertion of =0 in place of two hydrogen atoms. This is straightforward when the parent carries a CHz group at the appropriate position (example 206), but often the insertion of =0 requires prior reduction of a double bond. When the prefix oxo- is employed, this is achieved by using the appropriate hydro- prefix terms (example 207). However, the suffix -one can be used without hydro , the required reduction being implied rather than overtly stated (example 208) if desired the position of the hydrogen atom introduced to accommodate the carbonyl can be indicated in parentheses (see also examples 123 and 124). 

The p-cyanobenzyl ether, prepared from an alcohol and the benzyl bromide in the presence of sodium, hydride (74% yield), can be cleaved by electrolytic reduction (—2.1 V, 71% yield). It is stable to electrolytic removal ( — 1.4 V) of a tritylone ether [i.e., 9-(9-phenyl-10-oxo)anthiyl ether]. ... 

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