ISSN:
0170-2041
Keywords:
Specionin analogs
;
(-)-3′-Methoxyspecionin
;
Iridoid glucosides, peracetylated
;
Cleavage of the glucoside bond, selective
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Chemistry and Stereochemistry of Iridoids XV. - An Efficient Synthesis of Enantiomerically Pure (-)-Specionin Analogs from Peracetylated Iridoid Glucosides. - Crystal and Molecular Structure of (-)-3′-MethoxyspecioninWhen peracetylated iridoid glucosides are submitted to hydroxymercuration and reduction with zinc the glucoside bond is cleaved exclusively. The aglycones can be regio- and stereoselectively transformed into specionin analogs. An example is the preparation of crystalline (-)-3′-methoxyspecionin (3b) from hexaacetyl-6-O-vanilloylcatalpol (1d), which is readily available in larger quantities. The stereochemistry of 3b was determined by X-ray crystallographic analysis.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199119910186
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