Complex metal hydride reduction of carbon-carbon unsaturation. I. Sodium borohydride reduction of .alpha.-phenylcinnamates and related systems

1974 ◽  
Vol 39 (6) ◽  
pp. 755-760 ◽  
Author(s):  
J. Herman Schauble ◽  
Gerald J. Walter ◽  
J. Guy Morin
Keyword(s):  
Sodium Borohydride ◽  
Metal Hydride ◽  
Borohydride Reduction ◽  
Complex Metal ◽  
Hydride Reduction ◽  
Sodium Borohydride Reduction

Flavan derivatives. XXXIII. 2-Methoxyflavan-3,4-dione and 2-Methoxyflavan-3,4-diol derivatives

1972 ◽  
Vol 25 (4) ◽  
pp. 857 ◽  
Author(s):  
JW Clark-Lewis ◽  
I Dainis ◽  
EJ McGarry ◽  
MI Baig
Keyword(s):  
Sodium Borohydride ◽  
Catalytic Hydrogenation ◽  
Room Temperature ◽  
Periodic Acid ◽  
Metal Hydrides ◽  
Borohydride Reduction ◽  
Complex Metal ◽  
Sodium Borohydride Reduction ◽  
A Minor ◽  
Minor Quantity

Sodium borohydride reduction of 3-hydroxy-7-benzyloxy-2,3,4'-trimethoxy-flavanone and of 3-hydroxy-2,3,7,4'-tetramethoxyflavanone is shown to yield mainly trans-trans-2-methoxyflavan-3,4-dials, a novel class of flavan derivatives. The 7-benzyloxy hemiacetal also gave a minor quantity of the cis-cis-2-methoxyflavan-3,4-dial and less of the corresponding 2,3-cis-flavan-3,4-trans-dial. Catalytic hydrogenation over palladium, or reduction with complex metal hydrides at room temperature or above, converted the hemiacetals into the flavonols from which they were originally prepared by oxidation with periodic acid in methanol.

The structure and function of oestrogens. V. Synthesis of (9,12,12-2H3)- and (11ζ 12,12-2H3)-oestradiol

1983 ◽  
Vol 36 (2) ◽  
pp. 403 ◽  
Author(s):  
DJ Collins
Keyword(s):  
Acid Hydrolysis ◽  
Sodium Borohydride ◽  
Structure And Function ◽  
Borohydride Reduction ◽  
Hydride Reduction ◽  
Biological Studies ◽  
Sodium Borohydride Reduction ◽  
And Function ◽  
Hydrolysis Of

17,17-Ethylenedioxy-3-methoxy(9,12,12-2H3)-9β-oestra-l,3,5(10)-trien-11-one (3) was reduced to the mixture of 11-epimeric alcohols (4) which upon elimination of DHO gave the (12,12-2H2)-9(11)- dehydrooestrone derivative (5b). Treatment of (5b) with (2H6)diborane followed by oxidation afforded the (9,12,12-2H3)alcohol (8a); hydride reduction of the corresponding tosylate then gave 17,17-ethylenedioxy-3-methoxy(9,12,12-2H3)oestra-l,3,5(l0)-triene (7). Acid hydrolysis of (7), followed by demethylation, and reduction with sodium borohydride yielded (9,12,12-2H3)oestradiol (10). Sodium borohydride reduction of (11&12,12-2H3)oestrone (6),prepared in several steps from the 9β,12,12-trideutero ketone (3), gave (11 ξ,12,12-2H3)oestradiol (9). [The two trideuterated oestradiols (9) and (10) were required for biological studies.]

Stereoselective synthesis of α-bulnesene, 4-epi-α-bulnesene, and 5-epi-α-bulnesene

1970 ◽  
Vol 48 (14) ◽  
pp. 2234-2245 ◽  
Author(s):  
Edward Piers ◽  
Kin Fai Cheng
Keyword(s):  
Sodium Borohydride ◽  
Lithium Aluminum Hydride ◽  
Stereoselective Synthesis ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Borohydride Reduction ◽  
Similar Sequence ◽  
Hydride Reduction ◽  
Photochemical Rearrangement ◽  
Sodium Borohydride Reduction

Lithium–ammonia reduction of the hydroguaiazulene derivative 6, followed by oxidation of the resulting diol 13, gave, in a highly stereoselective manner, the keto alcohol 14. The latter was converted into 5-epi-α-bulnesene (2). In a similar sequence of reactions, 4-epi-α-bulnesene (3) was obtained from compound 9. Photochemical rearrangement of the previously obtained dienone 25 gave the hydroguaiazulene derivative 27. Successive subjection of the latter to acetylation, hydrogenation, and sodium borohydride reduction gave a mixture of the epimeric diols 31 and 32. When this mixture was treated with p-toluenesulfonic acid in pyridine, and the resulting olefinic diester 35 was sequentially subjected to hydrogenation [tris(triphenylphosphine)chlororhodium] and lithium aluminum hydride reduction, the crystalline diol 37 was obtained. The latter was converted into α-bulnesene (1) by standard reactions.

scholarly journals FACILE PREPARATION OF PLATINUM SOLS BY SODIUM BOROHYDRIDE REDUCTION AND ITS EVALUATION IN THE PHOTOSENSITIZED REDUCTION OF WATER TO HYDROGEN

1983 ◽  
Vol 12 (6) ◽  
pp. 893-896 ◽  
Author(s):  
Yohmei Okuno ◽  
Yukihiro Chiba ◽  
Osamu Yonemitsu
Keyword(s):  
Sodium Borohydride ◽  
Borohydride Reduction ◽  
Sodium Borohydride Reduction ◽  
Facile Preparation

1,2-Benzothiazines. II. The Preparation and Sodium Borohydride Reduction of 3-Acyl-2H-1,2-benzothiazin-4(3H)-one 1,1-Dioxides1

1965 ◽  
Vol 30 (7) ◽  
pp. 2241-2246 ◽  
Author(s):  
Harold Zinnes ◽  
Roger A. Comes ◽  
Francis R. Zuleski ◽  
Albert N. Caro ◽  
John Shavel
Keyword(s):  
Sodium Borohydride ◽  
Borohydride Reduction ◽  
Sodium Borohydride Reduction
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