C-glycosidic adriamycin analogs

Details C-glycosidic adriamycin analogs C-glycosidic adriamycin analogs

1984-11-23

1987-11-10

Griffin, Ronald W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 187, 536 552, 536 553, 536124, C07H 702, C07H 1524

Patent

active

047058501

ABSTRACT:
Disclosed herein is a new procedure for preparing the C.1-2,4-pentadienyl derivatives of 2-deoxyhexopyranoses, as well as a new procedure for allylation of daunosamine. These methods are particularly useful for the preparation of intermediates in the synthesis of adriamycin C-glycosidic analogs which are useful anti-tumor agents. These methods provide the first enabling disclosure of methods to prepare these desired adriamycin and anthrocyclinone C-glycosidic analogs.

REFERENCES:
patent: 2746956 (1956-05-01), Speier
patent: 4446312 (1984-05-01), Noyori et al.
patent: 4464529 (1984-08-01), Mosher et al.
Acton, E. M. et al., Tetrahedron Letters, (1984) 25:5743-5746.
Acton, E. M. et al., Carbohyde., Res., (1981) 97:235-245.
Chandler, M. et al., (1980), J.C.S. Perkin I., 1007-1012.
Kozikowski, A. P. et al., (1983), Tetra. Letters, 24:1563-1566.
Lewis, M. D. et al., (1982), J. Am. Chem. Soc., 104:4976-4978.

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