Total synthesis of 8,12-iso-iPF3alpha-VI, an EPA-derived isoprostane: stereoselective introduction of the fifth asymmetric center.
[reaction: see text] A new and stereoselective approach for the synthesis of all-syn isoprostanes is reported. This method, which is based on acid-catalyzed Diels-Alder reaction, allows the introduction of the side chain with a predetermined stereochemistry of the hydroxy group. The first total synthesis of an eicosapentaenoic acid (EPA)-derived iP, 8,12-iso-iPF3alpha-VI 10, was performed using this approach.
Jacobo
Sheila H
SH
Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901, USA.
Chang
Chih-Tsung
CT
Lee
Gue-Jae
GJ
Lawson
John A
JA
Powell
William S
WS
Pratico
Domenico
D
FitzGerald
Garret A
GA
Rokach
Joshua
J
D002384:Catalysis; D015118:Eicosapentaenoic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D006900:Hydroxylation; D028421:Isoprostanes / Q000138:chemical synthesis*; D013237:Stereoisomerism
C515332:8,12-iso-iPF3alpha-VI; D028421:Isoprostanes; D015118:Eicosapentaenoic Acid