The Determination of Complex Formation in Mixed Solvents by Gas Chromatography. The Tetrahydrofuran Complexes of Lithium Aluminum Hydride, Magnesium Bromide, and Several Grignard Reagents

1962 ◽  
Vol 1 (4) ◽  
pp. 921-925 ◽  
Author(s):  
Lloyd V. Guild ◽  
C. A. Hollingsworth ◽  
Darl H. McDaniel ◽  
Sunil Kumar Podder





1978 ◽  
Vol 56 (10) ◽  
pp. 1368-1371 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Hing-Kwok Hung ◽  
George L. Mhehe ◽  
M. L. Duarte Weinberg

Se lective thioketalization of a mixture of keto esters 5 and 6 resulted in the exclusive formation of thioketal 7 and complete recovery of keto ester 6. Lithium aluminum hydride reduction of thioketal 7 followed by Moffatt oxidation of the resulting alcohol 8 gave aldehyde 10 which on treatment with a mixture of cis- and trans-1-propenyl magnesium bromide afforded trans- alcohol 11 and its cis isomer 12. Manganese dioxide oxidation of alcohol 11 followed by desulfurization gave trans α-damascone (3). Similarly, alcohol 12 was converted to cis-α-damascone (4).



1948 ◽  
Vol 20 (4) ◽  
pp. 311-312 ◽  
Author(s):  
J. A. Krynitsky ◽  
J. E. Johnson ◽  
H. W. Carhart


1950 ◽  
Vol 22 (2) ◽  
pp. 364-365 ◽  
Author(s):  
B. B. Baker ◽  
W. M. MacNevin


1991 ◽  
Vol 69 (5) ◽  
pp. 772-778 ◽  
Author(s):  
Youla S. Tsantrizos ◽  
Kelvin K. Ogilvie

The antifungal antibiotic pisolithin B (p-hydroxymandelic acid, 2-(4′-hydroxyphenyl)-2-hydroxyethanoic acid, 1a) was shown to have the absolute (R) configuration. The stereochemistry was established via comparison of its optical rotation to that of its synthetic (R) and (S) enantiomers. The synthetic samples were prepared by the stereospecific reduction of the prochiral α-keto acid, p-hydroxybenzoylformic acid (2-(4′-hydroxyphenyl)-2-oxoethanoic acid, 2a), with (R) or (S)-2,2′-dihydroxy-1,1′-binaphthyl lithium aluminum hydride (BINAL-H). The absolute configuration and enantiomeric purity of both products were determined using the 1H NMR of their isobutyl esters in the presence of the chiral solvating agent (R)-(−)-2,2,2-trifluoro-1-(9-anthryl)ethanol. Key words: pisolithin B, p-hydroxymandelic acid, antifungal, absolute configuration.



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