First total synthesis of the E type I phytoprostanes |
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Affiliation: | Department of Cell Biology, University of Medicine and Dentistry of New Jersey, SOM, Stratford, NJ 08084, USA |
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Abstract: | The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxycyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. |
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Keywords: | phytoprostanes hydrolytic kinetic resolution protonation Takai reaction enzyme reactions |
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