Synthesis of new 1-C-(2-furyl)-and 3-C-(2-furyl)-hexopyranosides and 3-C-(2-furyl)-daunorubicin analogs

Summary Reaction of furan with 3,4-di-O-acetyl-L-rhamnal (1) afforded a mixture of epimeric 3-C-(2-furyl) glycals3 and4 and 1-C-(2-furyl)-hex-2-enopyranoses5 and6. Glycals3 and4 were transformed to 2-deoxy-glycosides9–13 and 3-deamino-3-C-(2-furyl)daunorubicines15 and16. Hex-2-enopyranosyl5 wascis hydroxylated with osmium tetroxide/N-methylmorpholine N-oxide to C-glycoside14.On leave from Pharmaceutical Research Institute, Warsaw, Poland