76917-15-2Relevant articles and documents
Synthesis of Malyngolide, an Antibiotic from the Marine Blue-Green Alga Lyngbya majuscula Gomont
Cardillo, Giuliana,Orena, Mario,Porzi, Gianni,Sandri, Sergio
, p. 2439 - 2442 (1981)
Malyngolide (1) was synthetized, starting from the condensation of dianion 2, obtained by metalation with lithium diisopropylamide of the sodium salt of tiglic acid, and decanal.Successive esterification of 3a and oxidation with Jones reagent of 4a afforded 5 in very good yield.Olefination of 5 with methylenemagnesium iodide gave 6, which was converted to the corresponding iodolactone 7.Hydrolysis of 7 to 1 was accomplished by Hg(ClO4)2 in dimethoxyethane/water (path A).Malyngolide (1) was also obtained by condensation of 2 with2-tetrahydropyran (9b).Removal of the THP protecting group in 10 by 6 N HCl affords 1 (path B).
Stability of diazocarbonyl compounds under the conditions of gas chromatography and chromatography-mass spectrometry analysis
Kornilova,Ukolov,Kostikov,Zenkevich
, p. 1675 - 1685 (2013/02/23)
The gas chromatographic analysis of alkyldiazoacetates N 2CHCO2R (R = CH3 - C4H9), α-aliphatic diazoketones RCOCHN2 (R = C3H 7, C5H11, and C9H19), and aryl-substituted diazoketones Ph (CH2)nCOCHN2 (n = 0-2) is shown to be possible when their retention temperatures are below the boiling points of compounds of this series at atmospheric pressure without decomposition (about 140°C). At higher temperatures occurs partial or complete decomposition of α-diazoketones in chromatographic columns to form ketenes. Among the impurities in the reaction mixtures at the diazotization of corresponding alkyl glycinates were identified for the first time the nitrate esters of glycolic acid O2NOCH2CO2R, as well as the dimeric products. All diazocarbonyl compounds and the impurities were characterized by mass spectra. For the first time their gas chromatographic retention indices were determined. Pleiades Publishing, Ltd., 2012.
