180348-00-9Relevant academic research and scientific papers
Synthesis of γ-Fluoro-α,β-unsaturated Carboxylic Esters from Saturated α-Fluoro Aldehydes
Oldendorf, Jens,Haufe, Gu?nter
, p. 52 - 57 (2000)
γ-Fluoro-α,β-unsaturated carboxylic esters 7a, 7b and 7d and 4-fluoro-4-phenylbut-3-enoic ester (8) are obtained by two alternative pathways from 2-fluoro aldehydes 5a-d, either by Horner-Wadsworth-Emmons reaction or by Wittig reaction. The aldehydes 5a-d are prepared by Swern oxidation of the corresponding fluorohydrins 4a-d. These are available from α-olefins by bromofluorination, bromine-by-acetate replacement and subsequent hydrolysis.
Synthesis of a fluorinated ether lipid analogous to a platelet activating factor
Haufe, Guenter,Burchardt, Annegret
, p. 4501 - 4507 (2001)
The synthesis of racemic 2-fluoro-3-hexadecyloxy-2-methyl-prop-1-yl 2′-(trimethylammonio)ethyl phosphate (10), a fluorinated analogue of the anticancer active and blood platelet activating ether lipids 8 and 9, has been achieved in a six-step sequence from methallyl alcohol (11). Etherification of 11 with hexadecyl bromide gave allylic ether 12, bromofluorination of which afforded the bromo-substituted fluoride 13, which was subsequently transformed into the acetate 14. Hydrolysis of 14 gave the key intermediate 2-fluoro-2-(hexadecyloxymethyl)propanol (15), which was attached to the phosphocholine residue in the final step. Enzyme-catalyzed deracemization of the fluorohydrin 15 by acetylation with several lipases gave optically active compounds 14 and 15, with a maximum ee of 61% for 15 with Candida antarctica lipase catalysis after 74% conversion. An enantioselective synthesis of 10, based on a planned eight-step synthesis starting from α-methylstyrene, failed. The anticancer activity of racemic 10 has been observed in an in vivo model of methylcholanthrene-induced mouse fibrosarcoma.
New synthetic routes to 2-fluoro-2-phenylalkanoic acids
Goj, Olav,Haufe, Guenter
, p. 1289 - 1294 (2007/10/03)
2-Fluoro-2-phenylalkanoic acids 2 are obtained by oxidation of the corresponding β-fluoro-β-phenyl alcohols 6. These compounds are shown to be accessible by two alternative pathways, either by bromo fluorination of α-alkyl styrenes 3, subsequent bromine-b
