ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Two methods for stereoselective β-glycosylation of digitoxose were developed. The first achieved stereocontrol by a 1,3-participation of a N-methylurethane group under acid catalysis. The second utilized mercuric-ion catalyzed cleavage of thioglycosides and a 1,3-participation of a p-methoxybenzoyl group in a neutral medium. The first highly stereoselective and quite efficient synthesis of digitoxin (C7) was achieved by a combination of these methods. The furyl-substituted precursor IV of digitoxigenin (Scheme 1) was used as aglycone, and the furan group was converted to the unsaturated lactone of digitoxin by our known oxidation procedure (m-chloroperbenzoic acid/NaBH4) after the assembly of the carbohydrate portion of the molecule and its deblocking was completed.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680203