Total synthesis of tylonolide, the aglycone of the 16-membered ring macrolide tylosin, from D-glucose. Selective application of MPM and DMPM protecting groups for hydroxy functions
✍ Scribed by Tatsuyoshi Tanaka; Yuji Oikawa; Tatsuo Hamada; Osamu Yonemitsu
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 286 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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 ring macrolide antibiotic that is important not only as a therapeutic agent but also as a target molecule in modern synthetic organic chemistry. In connection with our synthetic study of macrolide and polyether antibiotics from D-glucose by a common methodology consisting of stereocontrolled reactions and the MPM (4-methoxybenzyl) protection,2 a highly stereoselective and efficient synthesis of methynolide, the aglycone of the 12-membered ring macrolide methymycin, was recently achieved.' This methodology has been successfully applied to the total synthesis of tylonolide (1),3 the aglycone of tylosin. The general synthetic strategy consists of condensation and cyclization of segments i (2) and ii