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An efficient synthesis of 2,3-disubstituted tetrahydropyrans from aldehyde and cyclopropyl alkenol has been accomplished using HBF4·OEt2 as a promoter through a tandem vinylcyclopropane ring-opening/Prins cyclization. It is a convenient process to generate a structurally diverse and biologically relevant 2,3-disubstituted tetrahydropyrans in good yields with high selectivity.
A novel Prins/Friedel–Crafts cyclization of (Z)-6-(1-methyl-1H-indol-3-yl)hex-3-en-1-ol with aldehydes has been achieved using a catalytic amount of BF 3 ·OEt 2 under mild reaction conditions to produce the corresponding octahydropyrano[4,3-a]carbazole derivatives in good yields with high diastereoselectivity. The cross-coupling of (Z)-6-(1-methyl-1H-indol-3-yl)hex-3-ene-1-thiol with...
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