Novel synthesis of vinyl cyclopropane carboxylic acids: Application to the synthesis of (d,l)- and (d)-cis-chrysanthemic acid
β Scribed by Alain Krief; Dominique Swinnen
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 190 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
Methyl (d,l) trans-chrysanthemate as well as its cis-diastereoisomer have been prepared from dimethyl dimedone, one of their isomers, in a few steps and with complete control of the relative stereochemistry.
The decarbonylation of the bicyclic a-tertiary carboxamido acid 11 led to the enamide 12, easily transformed into the indolizidine alkaloid 8,8a-trans-8-hydroxy-indolizidine 14. Likewise, the same process applied to the Β’t-substituted pipecolic acid derivative 5 led to the unsaturated ester 6 which
Radicals generated by photofysis YW light1 of suitubly protected amino-acid derivutives of ~-hydroxy-~-thjopyr~done add efficientiy to o&voted olefins to offord ?otisfoctory yields of adducts, Ox~datiun of the thjopyridy~ residue to sulphoxide and thermol e~iminotion afford excellent yidds of the co