Synthesis of optically active deacetyl anisomycin

1968 ◽  
Vol 46 (19) ◽  
pp. 3091-3094 ◽  
Author(s):  
C. M. Wong ◽  
J. Buccini ◽  
J. Te Raa
Keyword(s):  
Tartaric Acid ◽  
Grignard Reagent ◽  
Sodium Ethoxide ◽  
Phosphorus Pentachloride ◽  
Optically Active ◽  
Epoxide Ring ◽  
Hydride Reduction ◽  
Lithium Aluminium ◽  
Basic Hydrolysis ◽  
Layer Chromatography

Optically active (−)-deacetyl anisomycin and the enantiomer (+)-deacetyl anisomycin were synthesized starting with (+)-2R 3R tartaric acid. The asymmetric centers of the tartaric acid correspond to the C-2 and C-3 asymmetric centers of anisomycin. N-Benzyl tartarimide (3) was attacked by the Grignard reagent of anisyl chloride followed by lithium aluminium hydride reduction to give two diols (7) and (8) separated by thin-layer chromatography. The diol (8) was debenzylated giving the natural (−)-deacetyl anisomycin. The diol (7) was converted into the epoxide (10) by selective acetylation of the C-4 hydroxy group followed by treatments with phosphorus pentachloride and sodium ethoxide. Opening of the epoxide ring of 10 in boiling acetic acid followed by basic hydrolysis gave (+)-N-benzyl deacetyl anisomycin (11) which was debenzylated to give (+)-deacetyl anisomycin.

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).

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.

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.

Synthesis of optically active macrolides with hydrazide fragments from tetrahydropyran and L-(+)-tartaric acid derivatives

2013 ◽  
Vol 49 (4) ◽  
pp. 691-693 ◽  
Author(s):  
G. Yu. Ishmuratov ◽  
M. P. Yakovleva ◽  
G. R. Mingaleeva ◽  
M. A. Shutova ◽  
R. R. Muslukhov ◽  
...  
Keyword(s):  
Tartaric Acid ◽  
Optically Active ◽  
Tartaric Acid Derivatives
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