Cross metathesis as a general strategy for the synthesis of prostacyclin and prostaglandin analogues.
[reaction: see text] A cross metathesis (CM) approach has been successfully applied to introduce fully functionalized omega-side chain appendages of various prostacyclin and prostaglandin analogues, resulting in high (E)-selectivities for the C13-C14 double bond and leading to the total syntheses of isocarbacyclin, 15R-TIC, carbacyclin, and PGF(2)(alpha) and the formal syntheses of 15-deoxy-TIC and PGJ(2).
Sheddan
Neil A
NA
Institut für Organische Chemie, Wien, Austria.
Mulzer
Johann
J
D011464:Epoprostenol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D015394:Molecular Structure; D015230:Prostaglandin D2 / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
C401841:15-deoxy-16-m-tolyl-17,18,19,20-tetranorisocarbacyclin; C037112:9-deoxy-delta-9-prostaglandin D2; C026678:carboprostacyclin; D011464:Epoprostenol; D015230:Prostaglandin D2