General strategy for the synthesis of B1 phytoprostanes, dinor isoprostanes, and analogs.
The synthesis of the phytoprostane B1 types I and II is achieved in high overall yield (35-53%) by only two principal transformations starting from 1,3-cyclopentanedione. The first side chain is attached via O-acylation of the 1,3-dione followed by rearrangement and reduction to give the 2-alkyl-1,3-diones 4a-c. After conversion into the corresponding vinylic iodides 5a-c, the second side chain is introduced by transition metal catalysis following Heck- or Sonogashira-type protocols. The whole spectrum of the phytoprostane B1 types I, II, and the dinor isoprostane B1 type III and some structural analogs are rapidly accessible along the same general protocol.
Schmidt
Annika
A
Department of Bioorganic Chemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll-Strasse 8, D-07745 Jena, Germany.
Boland
Wilhelm
W
D000215:Acylation; D000478:Alkylation; D002384:Catalysis; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D028421:Isoprostanes / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis
D005231:Fatty Acids, Unsaturated; D005663:Furans; D007202:Indicators and Reagents; D028421:Isoprostanes; D014753:Vinyl Compounds; C500684:phytoprostane B1 type I; C500683:phytoprostane B1 type II