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Abstract

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Paper | Special issue | Vol 28, No. 2, 1989, pp. 951 - 956
Published online:
DOI: 10.3987/COM-88-S108
Use of the Barton Decarboxylation Procedure in Indole Alkaloid Chemistry

Philip Magnus,* Mark Ladlow, Chung Sook Kim, and Peter Boniface

*Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, IN 47405-7102, U.S.A.

Abstract

L-Tryptophan was condensed with dimethyl α-ketoglutarate to give the tetracyclic amide (+) 8 and its diastereoisomer (-) 9. Conversion of (+) 8 into its derived N-hydroxy-2-thiopyridone ester 11 followed by t-butylthiol/hu gave (+) 12. This was converted into the desired tetracyclic amine (+) 2 in 30% overall yield. Similarly, starting with D-tryptophan gave (-) 2, thus allowing access to both antipodes of 2.

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