Synthesis of 3-deoxy-3,4-didehydro derivatives of 5-O-mycaminosyltylonolide, 5-O-(4-deoxymycaminosyl) tylonolide, and desmycosin.
The 3-deoxy-3,4-didehydro derivatives of 5-O-mycaminosyltylonolide, 5-O-(4-deoxymycaminosyl)tylonolide, and desmycosin have been prepared by treatment of the corresponding 3-O-sulfonyl derivatives with NaI in 2-butanone as the key step. The mechanistic difference in the formation of the 2,3- and 3,4-unsaturated derivatives from the same 3-O-sulfonyl derivative is discussed.
Kageyama
S
S
Institute of Bioorganic Chemistry, Kawasaki, Japan.
Tsuchiya
T
T
Umezawa
S
S
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015645:Tylosin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D000900:Anti-Bacterial Agents; C052318:tylosin B; C032963:4'-deoxymycaminosyltylonolide; D015645:Tylosin