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Communication | Regular issue | Vol 36, No. 8, 1993, pp.1735-1738
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6402
Functionalization at C-3a of Tryptophan Derived Hexahydropyrrolo[2,3-b]indoles

Milan Bruncko, David Crich,* and Raghu Samy

*University of Illinois at Chicago, Department of Chemistry (M/C 111), 801 West Taylor St. , Chicago, IL 60607-7061, U.S.A.

Abstract

Under free radical conditions the cyclic tryptophan tautomer (1) suffers oxidation at the benzylic position (C-3a) giving, with NBS, the 3a-bromo derivative and, with CAN, the 3a-hydroxy and 3a-nitrato derivatives. In contrast, under electrophilic conditions, aromatic bromination with NBS occurs cleanly at C-5