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• W2079461522 abstract "A fully stereocontrolled synthesis of 3-oxacarbacyclin (3) and a formal synthesis of carbacyclin (2) are described. The syntheses are based on the conjugate addition-azoalkene-asymmetric olefination strategy. Its key features are (1) the stereoselective establishment of the complete ω-side chain of 2 and 3 through conjugate addition of the enantiopure C13−C20 alkenylcopper derivative 10 to the enantiopure C6−C12 bicyclic azoalkene 9 and (2) the 5E-stereoselective construction of the α-side chain through a Horner−Wadsworth−Emmons olefination of the bicyclic ketone 7 with the chiral lithium phosphonoacetate 26 with formation of ester E-27. The allylic alcohol 6 serves at late stage as the joint intermediate in the synthesis of 2 and 3." @default.
• W2079461522 created "2016-06-24" @default.
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• W2079461522 date "2006-05-17" @default.
• W2079461522 modified "2023-10-07" @default.
• W2079461522 title "Fully Stereocontrolled Syntheses of 3-Oxacarbacyclin and Carbacyclin by the Conjugate Addition-Azoalkene-Asymmetric Olefination Strategy" @default.
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• W2079461522 doi "https://doi.org/10.1021/jo060551t" @default.
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