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Abstract Spiro[indolizidine-1,3′-oxindole] compounds have been synthesized in enantiomerically pure form from l -glutamic acid. The key oxidative ring contraction of chiral indolo[2,3-a]quinolizidinone was achieved by treatment with N-bromosuccinimide in tetrahydrofuran/water… Click to show full abstract
Abstract Spiro[indolizidine-1,3′-oxindole] compounds have been synthesized in enantiomerically pure form from l -glutamic acid. The key oxidative ring contraction of chiral indolo[2,3-a]quinolizidinone was achieved by treatment with N-bromosuccinimide in tetrahydrofuran/water in the presence of catalytic trifluoroacetic acid. The stereochemistry of the reaction was controlled by the dibenzylamino group which could be subsequently removed using Cope elimination.
Journal Title: Tetrahedron
Year Published: 2020
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