Tylosin total synthesis

Scheme 5. Ketophosphonate-aldehyde condensation in the total synthesis of a tylosin system.

When a stone is thrown into a pond, several waves are produced in succession, gradually spreading until they finally cover the whole pond. The stone in macrolide synthesis was the news that R.B. Woodward had started the total synthesis of erythromcyin A in 1973. Some waves are represented by Masamune s methymycin synthesis in 1975, Corey s erythronolide synthesis in 1978 and Tatsuta s carbomycin and tylosin syntheses in 1977 and 1981. One of the biggest waves is Woodward s erythromycin synthesis in 1981. 

Total syntheses of the following antibiotics and/or their aglycones are dealt with methymycin, erythromycin, pikromycin, oleandomycin, ingramycin (albo-cycline), carbomycin B, leucomycin A3 (josamycin), tylosin, mycinamicins, rosaramicin, A26771B and elaiophylin (azalomycin B). Since the total synthesis of the macrolide-like immunosuppressant FK-506 has been recently reported, it is also reviewed here. Today, erythromycin A, oleandomycin, leucomycin A3 (josamycin), tylosin and mycinamicin II are clinically important antibiotics. 

The first total synthesis of tylosin by regio- and stereoselective attachment of the sugar units (4-0-(o< -L-mycarosyl)- D-mycaminose... 

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