ISSN:
0170-2041
Keywords:
Hexaacetylaucubin
;
Palladium-catalysed substitution
;
Iridoidglucosides, N-containing
;
Carbohydrates
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Chemistry and Stereochemistry of Iridoids, XVII. - Palladium-Catalysed Substitution of HexaacetylacubinAcetoxy groups, in allylic position, can be replaced by nucleophiles in a palladium-catalysed reaction. The reaction of hexaacetylaucubin (2) with piperidine or benzylamine regioselectively gives the crystalline, N-containing iridoidglucosides 3 and 4. With the anion of diemethyl malonate, 5 was obtained along with the byproduct 7. Adding triethylammonium formate as a hydride donor, then the reaction gives 6; a reaction mechanism is discussed.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1991199101194
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