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- Title
A Reinvestigation of the Oxidative Rearrangement of Yohimbane-Type Alkaloids. Part A. Formation of pseudoindoxyl ( = 1,2-dihydro-3 H-indol-3-one) derivatives.
- Authors
Stahl, Reto; Borschberg, Hans-Jürg
- Abstract
Contrary to earlier reports, the base-induced rearrangement of the 7-hydroxy-7 H-indolenines derived from ajmalicine ( 1), yohimbine ( 5), corynanthine ( 6), methyl reserpate ( 16), and methyl isoreserpate ( 17) in each case furnished not just one, but two epimeric spiro-pseudoindoxyl derivatives which have opposite configuration at the spiro centre C(2). In all cases, the major component was shown by NOE experiments to be the A-type isomer (carbonyl group located below the plane defined by rings C and D). The thermodynamically less stable B-type pseudoindoxyl epimers 4, 10, 12, and 22 were isolated and characterized for the first time.
- Publication
Helvetica Chimica Acta, 1994, Vol 77, Issue 5, p1331
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19940770514