Total Synthesis of the Four Enantiomerically Pure Diasteroisomers of the Phytoprostanes E1Type II and of the 15-E2t-Isoprostanes.
Syntheses of the four enantiomerically pure diastereoisomers of the phytoprostanes E1 type II and 15-E2t-isoprostanes (1-4) are described. The key steps included the preparation of the Freïmanis (+/-)-hydroxycyclopentenone 5, enzymatic resolution of this racemic hydroxycyclopentenone, Wittig and Horner-Wadsworth-Emmons (HWE) coupling reactions and finally enantioselective reductions.
Pinot
Edith
E
Institut des Biomolécules Max Mousseron, IBMM, UMR CNRS 5247, Université Montpellier I, Université Montpellier II, Faculté de Pharmacie, 15. Av. Ch. Flahault, F-34093 Montpellier cedex 05, France.
Guy
Alexandre
A
Fournial
Anais
A
Balas
Laurence
L
Rossi
Jean-Claude
JC
Durand
Thierry
T
D003517:Cyclopentanes / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D028421:Isoprostanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D003517:Cyclopentanes; D028421:Isoprostanes; C007201:cyclopentanone; D006859:Hydrogen