PURPOSE: To efficiently obtain the subject antibiotic effective against gram-positive bacteria by directly methylating the 3"-hydroxyl group of a specific 16-membered ring macrolide derivative having the hydroxyl group at the 3" position as a starting raw material in mild conditions.
CONSTITUTION: This new method for efficiently producing a 16-membered ring macrolide derivative comprises protecting the 2'-hydroxyl group of medemycin, a 16-membered ring antibiotic of the formula (R1 is H, a 2-4C aliphatic acyl; R2 is a 1-4C aliphatic alkyl), as a starting raw material with an acetyl group, methylating the 3"-tertiary hydroxyl group of the mycarose portion with a methylating agent such as methyl triflate, treating the 3'-quaternary ammonium salt group simultaneously methylated by the reaction with a peroxide, reducing the one oxygen-imparted compound of formula II (X is triflate) with lithium iodide to return into the tertiary amino group, and subsequently converting the 9-protecting group, thus efficiently obtaining the objective derivative of formula III (R3 is H, a protecting group).
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SHIOKAWA NOBUE
AKIYAMA YOSHIHISA
USUI TAKAYUKI
