Total synthesis of tylosin

✍ Scribed by Kuniaki Tatsuta; Yoshiya Amemiya; Yoshinobu Kanemura; Hideaki Takahashi; Mitsuhiro Kinoshita

• Book ID: 104221064
• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 288 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87619-4

✦ Synopsis

Tylosln has been synthesized by reglo-and stereoselectlve lntroductlon of the amino dlsaccharlde moiety and D-mycrnose onto the previously synthesized 16-membered-ring aglycone. Tylosln (1)) a 16-membered-ring macrohde antlblotlc, IS extremely used as a therapeutrc substance in treatment of mycoplasmosls in poultry 1 An aglycone (2) of tylosln has been stereospeclflcally synthesized from D-glucose In these laboratories. 2 Herein, we report the first total 3 synthesis of tylosln (1) by reglo-and stereoselectlve lntroductron of the amino dlsaccharlde, namely 4-O-( CL -L-mycarosyl) -D-mycamlnose, and D-myclnose onto the C-5 and C-23 hydroxyl groups of the macrohde aglycone The synthesis began with the conversion of the aglycone 2 into the ethylene acetal 5 as previously described in the total synthesis of carbomycln B 4 Acid hydrolyses (4% H3P04 In 50% aq THF, 60°, hemlacetal 35 (78%, mp 120°, [a] 21h) of the aforesard 2 (mp 124O, [cr], +60°)5 afforded the D +25O), which was treated with ethylene glycol (TsOH, dloxane, 350, 2 days) to give the hydroxyethyl furanoslde 46 (62%, mp 118", [al, +53O) and 54 (ll%, mp 88O, LoI, +23", imax 284 nm (E 21400)) after preparative TLC (Rf 0 37 and 0.39, PhMe-hexane-Me2C0