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Total synthesis of tylonolide, an aglycone of tylosin

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

Book ID: 104234379
Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 326 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)82047-5

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✦ Synopsis

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 important 16membered-ring macrolide antibiotics.

the desired aglycone G3 (86%, mp 124" (needles), [a], +60", A::? 282 nm (E 21600)) identical in all respects with a naturally derived authentic sample. By this completion, the absolute configuration (especially at C14)2b of tylosin Q,) was confirmed.

Authentic samples of &, J_,Q and Q&,k were derived from tylosin (,J,) as follows.

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