Total synthesis of 15-D(2t)- and 15-epi-15-E(2t)-isoprostanes.
The first total synthesis of 15-D(2t)-isoprostane is described. (-)-(9S,15S)-15-D(2t)-IsoP 1 and (+)-(11R,15R)-15-epi-15-E(2t)-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of the cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules.
Brinkmann
Yasmin
Y
Institut des Biomolécules Max Mousseron, IBMM, UMR CNRS 5247, Université Montpellier I, Université Montpellier II, Faculté de Pharmacie, 15, avenue Charles Flahault, France.
Oger
Camille
C
Guy
Alexandre
A
Durand
Thierry
T
Galano
Jean-Marie
JM
D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D005656:Fungal Proteins; D028421:Isoprostanes / Q000138:chemical synthesis* / Q000737:chemistry; D008049:Lipase / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D005656:Fungal Proteins; D028421:Isoprostanes; D008049:Lipase; C431349:lipase B, Candida antarctica