Synthesis of spiro[indolizidine-1, 3′-oxindole] from l-glutamic acid. Issue 24 (12th June 2020)

• Record Type: Journal Article
• Authors: Kuntiyong, Punlop; Inprung, Nantachai; Phakdeeyothin, Kunita; Buaphan, Artid; Thammapichai, Kittisak
• Is Part Of: Tetrahedron. Volume 76:Issue 24(2020)
• Publication Date: 2020-06-12
• Subjects: Spiro[indolizidine-oxindole] -- Enantiomerically pure -- Synthesis -- l-glutamic acid -- Oxidative rearrangement; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131261
• Languages: English
• ISSNs: 0040-4020

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. Graphical abstract: Image 1 Highlights: Synthesis of spiro[indolizidine-1, 3′-oxindole] in enantiomerically pure form from l -glutamic acid. Enantio- and diastereodivergent synthesis of four diastereomers of spiro[indolizidine-1, 3′-oxindole]. Synthetic spiro[indolizidine-1, 3′-oxindole] with functionalities suitable for further manipulations.