Synthesis of tylonolide, the aglycone of tylosin
โ Scribed by Masamune, Satoru; Lu, Linda D. L.; Jackson, William P.; Kaiho, Tatsuo; Toyoda, Tatsuo
- Book ID
- 126934174
- Publisher
- American Chemical Society
- Year
- 1982
- Tongue
- English
- Weight
- 516 KB
- Volume
- 104
- Category
- Article
- ISSN
- 0002-7863
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๐ SIMILAR VOLUMES
Segments i (Cll-C17) and ii (Cl-ClO), synthesized from D-glucose by employing some stereoselective reactions and benzyl-type protecting groups, were esterified and cyclized to the 16-membered enone, which was readily converted to tylonolide, the aglycone of tylosin. Tylosin is a typical 16-membered
The total synthesis of tylonolide, a 16-membered-ring aglycone of a macrolide antibiotic, tylosin, has been accomplished by coupling two segments of Cl-Cl0 and Cll-Cl7 portions, which are stereospecifically derived from D-glucose. Josamycin (leucomycin A3) and tylosin (4) constitute the medicinally
The synthesis of the lactonic thioester 5, corresponding to the C(l)-C( 9) fragment of tylonolide hemiacetal, via the bicyclic ester 5 , is described.
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 mycoplas