ISSN:
0170-2041
Keywords:
Anthracycline glycosides
;
Allylic rearrangement
;
Glycosylation
;
NIS procedure
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
In Lewis acid mediated allylic rearrangement reactions of L-rhamnal (1) and L-fucal (2) with daunomycinon (6) 2′-deoxyhex-2′-enopyranosides have been obtained exclusively. Furthermore, glycals 1 and 4 have been treated with the glycosyl acceptors 6, 7, and 9 and N-iodosuccinimide (NIS) to produce the corresponding α-configurated 2′-deoxy-2′-iodo glycosides. Among these, 16 represents a bis (glycoside) with both benzylic aglycon positions substituted. In none of the above cases has a substantial amount of β-glycoside been detected. Attempts to convert ε-isorhodomycinon (8) into a glycoside on a preparative scale, under Lewis acid conditions have been unsuccessful. However, the α-glycoside 13 has been obtained by the Helferich method.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199119910193
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