Convergent stereospecific total synthesis of Monocillin I and Monorden (or Radicicol)

The first total syntheses of the antifungal resorcylic macrolides Monocillin I and Monorden (or Radicicol) have been achieved by a convergent stereospecific route. TBDMS phenol ethers were found to be suitable for all the scheme and were removed in the ultimate step under mild conditions (aqueous bo...

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Veröffentlicht in:Tetrahedron letters 1992-02, Vol.33 (6), p.777-780
Hauptverfasser: Lampilas, Maxime, Lett, Robert
Format: Artikel
Sprache:eng
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Zusammenfassung:The first total syntheses of the antifungal resorcylic macrolides Monocillin I and Monorden (or Radicicol) have been achieved by a convergent stereospecific route. TBDMS phenol ethers were found to be suitable for all the scheme and were removed in the ultimate step under mild conditions (aqueous borax/THF/methanol), hence allowing to get the natural macrolides in good yields, with no degradation. An efficient conversion of di-OTBMDS Monocillin I into Monorden is also reported. [Display omitted]
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)77713-6