ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Contrary to earlier reports, the base-induced rearrangement of the 7-hydroxy-7H-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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19940770514