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• W2079502520 endingPage "193" @default.
• W2079502520 startingPage "179" @default.
• W2079502520 abstract "The most general method available for synthesis of chiral long-chain compounds is based on chain extension of completely resolved precursors. A large number of optically pure compounds may thus be prepared from a small number of chiral key molecules, and resolution steps, uncertain and often laborious, are few, or may be avoided if an optically active natural product is used as starting material.86 Pioneering and extensive work in the field was carried out by the Stenhagens from the middle of the 1940s. They started by synthesizing branched-chain fatty acids,1*73 and began experiments with hydroxy compounds in 1950. At that time, it had been found convenient to use the anodic Kolbe reaction for chain extension of optically active carboxylic acids with branching beyond the or-position,‘*s2*7s and they then tried 3-hydroxybutanoic acid in a Kolbe synthesis. 68 When difficulties arose because of skin formation at the electrodes, the acetate was tried instead, and found to react normally.68 They initiated its resolution by means of quinine, and then asked me to continue the work. At the same time, they proposed that a key molecule allowing chain extension in both directions should be synthesized, and suggested an acetylated monoester of 3-hydroxyglutaric acid.68 This review briefly outlines the preparation of twelve key molecules (1-12, enantiomers included) and lists some fifty long-chain hydroxy compounds synthesized from them. A few new compounds (4d, 11, lla) are included, and previously unpublished physical data have been added for some known compounds (6a, 7a, b, d). Prominent features and compounds of special interest are commented on. Other reviews do not overlap with the present one to any great extent. It has most in common with a survey of optically active long-chain natural compounds by C. R. Smith,” published in 1970, and with a chapter on use of the Kolbe electrosynthesis for assignment of absolute configuration by J. H. Brewster,“” published in 1972. Information from readers concerning errors and new or overlooked compounds and publications belonging to the field under review will be appreciated." @default.
• W2079502520 created "2016-06-24" @default.
• W2079502520 creator A5071175595 @default.
• W2079502520 date "1978-01-01" @default.
• W2079502520 modified "2023-09-27" @default.
• W2079502520 title "Optically active higher aliphatic hydroxy compounds synthesized from chiral precursors by chain extension" @default.
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• W2079502520 doi "https://doi.org/10.1016/0079-6832(78)90043-5" @default.
• W2079502520 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/358264" @default.
• W2079502520 hasPublicationYear "1978" @default.
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