Chemistry of the Podocarpaceae. XXXVII. Oxidative degradations of phyllocladene and isophyllocladene : conversion of isophyllocladene into (+)-Podocarp-8(14)-en-13-one

1972 ◽  
Vol 25 (5) ◽  
pp. 959 ◽  
Author(s):  
RC Cambie ◽  
RC Hayward
Keyword(s):  
Chromium Trioxide ◽  
Optically Active ◽  
Oxidative Decarboxylation ◽  
Lithium Aluminium Hydride ◽  
Keto Acid ◽  
Hydride Reduction ◽  
Lithium Aluminium ◽  
Villiger Oxidation

The ozonolysis of phyllocladene (2) and isophyllocladene (12) has been carried out under a number of different conditions and the ozonide (34) of isophyllocladene has been isolated and characterized. Conversion of phyllocladene (2) into the diacid (20) has been accomplished by several routes from the norketone (3). Isophyllocladene (12) has been converted into (+)-podocarp-8(14)-en-13-one (1), an optically active relay which is useful in synthesis. The route involves ozonolysis of isophyllocladene, Baeyer-Villiger oxidation of the keto aldehyde (25), lithium aluminium hydride reduction of the ester (27), and chromium trioxide-pyridine oxidation of the resulting keto aldehyde (32) which gives the keto acid (30) in 26% overall yield. Oxidative decarboxylation then affords the enone (1) in 14% yield.

Studies of the optically active compounds of Anacardiaceae Exudates. IV. The structures of the rearrangement products from the long chain alicyclic ketoalocohol of Tigaso oil in Alkali

1958 ◽  
Vol 11 (4) ◽  
pp. 538
Author(s):  
JA Lamberton
Keyword(s):  
Methyl Ether ◽  
Active Compound ◽  
Monomethyl Ether ◽  
Optically Active ◽  
Side Chain ◽  
Lithium Aluminium Hydride ◽  
Active Compounds ◽  
Hydride Reduction ◽  
Lithium Aluminium ◽  
Long Chain

The structure IIIa previously proposed for the β-diketone with an unsaturated side chain, obtained by the action of alkali on the optically active compound of Tigaso oil, is confirmed by the formation of methyl stearyl ketone and resorcinol monomethyl ether in the pyrolysis of the methyl ether (IV). An anomalous lithium aluminium hydride reduction of the methyl ether (IV) and other reactions are discussed. Unsuccessful attempts have been made to synthesize the tribasic acid resulting from sodium hypobromite oxidation of the β-diketone (IIIb).

Attempted Enantioselective Synthesis of Terbutaline. Unexpected Partial Racemization During Lithium Aluminum Hydride Reduction of a Secondary Amide

1995 ◽  
Vol 48 (10) ◽  
pp. 1741 ◽  
Author(s):  
AC Donohue ◽  
WR Jackson
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Lithium Aluminum ◽  
Secondary Amide ◽  
Lithium Aluminium Hydride ◽  
Hydride Reduction ◽  
Lithium Aluminium

Syntheses leading to compounds related to the bronchodilator (–)- terbutaline via optically active cyanohydrins suffered unexpected partial racemization during lithium aluminium hydride reduction of key amide intermediates.

Studies on epoxides. Part II. Abnormal lithium aluminium hydride reduction of cis 3,4-epoxy-5-hydroxycholestanes

1967 ◽  
Vol 8 (52) ◽  
pp. 5261-5263 ◽  
Author(s):  
E. Glotter ◽  
S. Greenfield ◽  
D. Lavie
Keyword(s):  
Lithium Aluminium Hydride ◽  
Hydride Reduction ◽  
Lithium Aluminium

1-[2-(2-Hydroxymethylphenylthio)benzyl]-4-methylpiperzine and related compounds as potential antidepressants: Synthesis and pharmacological acreening

1984 ◽  
Vol 49 (4) ◽  
pp. 1009-1020 ◽  
Author(s):  
Irena Červená ◽  
Miroslav Protiva
Keyword(s):  
Potassium Carbonate ◽  
Secondary Alcohol ◽  
The Other ◽  
Lithium Aluminium Hydride ◽  
Keto Acid ◽  
Open Model ◽  
Lithium Aluminium ◽  
Neuroleptic Agent ◽  
The One ◽  
Related Compounds

Heating of 1-(2-iodobenzoyl)-4-methylpiperazine (II) with thiophenol and its 2-methyl, 4-methyl, 4-chloro and 2-hydroxymethyl derivatives in dimethylformamide in the presence of potassium carbonate, copper and cuprous iodide gave the piperazides IV-VIII; compound VIII was transformed by reduction with lithium aluminium hydride to the title compound I. The acid IX, obtained by a reaction of 5-chloro-2-iodobenzoic acid with 2-methylthiophenol, was reduced to the alcohol X, which was transformed via the chloride XI to 1-[5-chloro-2-(2-methylphenylthio)-benzyl]-4-methylpiperazine (XII), an open model of the neuroleptic agent clorothepin. Heating of 2,5-dichloroacetophenone with thiosalicylic acid afforded the keto acid XIII whose reaction with 1-methylpiperazine was carried out with the help of N,N"-carbonyldiimidazole. The piperazide XIV obtained was reduced on the one hand with sodium borohydride to the secondary alcohol XV, and with lithium aluminium hydride to 1-(2-[4-chloro-2-(1-hydroxyethyl)phenylthio]benzyl)-4-methylpiperazine (XVI) on the other. None of the dibasic piperazines (I, XII, XVI) did show antireserpine activity. In the general screening, some of the piperazides displayed a mild hypotensive (II, VIII, XIV, XV), adrenolytic (VIII), mild stimulating and antitussic (V), and spasmolytic, antiinflammatory and negatively ino- and chronotropic (XIV) activities.

A Novel Synthesis of 1-Aryl-9-alkyl-2, 3, 3a, 4, 9, 9a-hexahydro-1H-pyrrolo[2, 3-b] quinoxalines by lithium aluminium hydride reduction of N-phenyl-1-benzimidazolyl-succinimides

1973 ◽  
Vol 56 (5) ◽  
pp. 1646-1655 ◽  
Author(s):  
Quazi Ahmed ◽  
Theodor Wagner-Jauregg ◽  
Ernst Pretsch ◽  
Josef Seibl
Keyword(s):  
Lithium Aluminium Hydride ◽  
Hydride Reduction ◽  
Lithium Aluminium ◽  
Novel Synthesis

Lithium aluminium hydride reduction of some organo-sulphur compounds.

1967 ◽  
Vol 8 (11) ◽  
pp. 971-974 ◽  
Author(s):  
Kazi Abdul Latif ◽  
Paritosh Kumar Chakraborty
Keyword(s):  
Lithium Aluminium Hydride ◽  
Sulphur Compounds ◽  
Hydride Reduction ◽  
Lithium Aluminium
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