Convergent processes for preparing macrolide antibacterial agents

A process for preparing a compound of formula (I)

• or a pharmaceutically acceptable salt thereof;
• wherein
• R1 is a desosamine or a desosamine derivative;
• A is —CH2—, —C(O)—, —C(O)O—, —C(O)NH—, —S(O)2—, —S(O)2NH—, or —C(O)NHS(O)2—;
• B is saturated C0-C10;
• or B is unsaturated C2-C10;
• or -A-B- taken together is alkylene, alkenylene, cycloalkylene, or arylene;
• C represents 2 substituents independently selected in each instance from the group consisting of hydrogen, halogen, hydroxy, acyl, acyloxy, sulfonyl, ureyl, and carbamoyl, and alkyl, alkoxy, heteroalkyl, aryl, heteroaryl, arylalkyl, and heteroarylalkyl, each of which is optionally substituted;
• and
• W is hydrogen, F, Cl, Br, I, or OH;
• the process comprising (A) contacting a compound of formula
• or a salt thereof, where R100 is a hydroxyl protecting group, and L is a leaving group, with a compound of formula
• or a salt thereof, where C is as defined herein, and CP is a protected form of C, and a base, to prepare a compound of formula
• or a salt thereof;
• or
• (C) contacting a compound of formula
• or a salt thereof, with an acid to prepare a compound of formula
• or a salt thereof;
• or
• (E) contacting a compound of formula
• or a salt thereof, with an oxidizing agent to prepare a compound of formula
• or a salt thereof;
• or
• (F) contacting a compound of formula
• or a salt thereof, with a hydroxylating or halogenating agent to prepare a compound of formula
• or a salt thereof, wherein W is F, Cl, Br, I, or OH;
• any combination of the foregoing.