Malic acid diethyl ester

The enantiomerically pure indolizidine (—)-422 has been synthesized starting from L-malic acid diethyl ester 407. The hydroxyl function of L-malic acid diethyl ester 407 has been protected as dihydropyranyl ether 408 with 2/7-dihydropyran and Amberlyst 15 in pentane at room temperature. The diethyl ester 408 was then reduced with lithium aluminium hydride in diethyl ether under reflux and the newly generated hydroxyl functions then protected with mesyl chloride in the presence of triethylamine in dichloromethane at 0°C. This was converted into newly protected pyrroline nitrone 409 in 44% overall yield through a well-established method (Scheme 90). The regio-isomeric 5-pyrroline-iV-oxide 410 formed in 4% overall yield was easily separated by column chromatography <20000L2475>. 

Diethyl S-malate Malic acid, diethyl ester, (S)- (8) Butanedioic acid, hydroxy-, diethyl ester, (S)- (9) (691-84-9)... 

CAS 626-11-9 EINECS/ELINCS 210-930-0 Synonyms Diethyl malate Ethyl malate DL-Malic acid diethyl ester... 

Maleimide, N-phenyl. See N-Phenylmaleimide Maleinic acid. See Maleic acid Maleinic resin. See Maleic resin Malenic acid. See Maleic acid N,N-Maleoylhydrazine. See Maleic hydrazide Malic acid (INCI). See N-Hydroxysuccinic acid DL-Malic acid diethyl ester. See Diethyl DL-malate... 

The C-17 to C-22 subunit of ionomycin (937) is synthesized by regioselective fragmentation of an appropriately substituted tetrahydrofuran (935), which is readily accessible from (R)-malic acid (Scheme 137) [205]. Alkylation of the dianion of diethyl (7 )-malate (897) with methyl iodide provides anti-929 in 69% yield with 10 1 stereoselectivity. Reduction of the esters, acetal formation, oxidation of the primary alcohol of 930 to an aldehyde, and Wittig olefination furnishes a,j -unsaturated ester 931. 

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