ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Oxindole 11, obtained on 3-[2′-(dimethylamino)ethyl]alkylation of oxindole 12, yielded, on stereoselective reduction with sodium dihydridobis(2-methoxyethoxy)aluminate, aminoalcohol 8 (Scheme 2). The quaternary methiodide 10, obtained from 8 with MeI, gave, in nucleophilic displacements concurring with a Hofmann elimination, (±)-esermethole 6, (±)-5-O-methylphysovenol (14), (±)-5-O-methyl-1-thiaphysovenol (15), and (±)-1-benzyl-1-demethylesermethole (16). Syntheses of (±)-1-benzyl-1-demethylphenserine (18), (±)-1-demethylphenserine (19), and (±)-phenserine (4) from 6 and 16 are described. Optically active 8a and 8b, obtained by chemical resolution, similarly gave the enantiomers 6a and 14a-16a of the (3aS)-series (prepared earlier from physostigmine (1a)) and their (3R)-enantiomers. The anticholinesterase activity of (±)-4, (±)-18, and (±)-19 was compared with that of their optically active enantiomers.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19940770519
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