Stereoselective synthesis of the cytotoxic macrolide aspergillide B

A stereoselective synthesis of the cytotoxic macrolide aspergillide B has been performed. The three key fragments A, B and C were connected with the aid of a cross metathesis (CRM), a Mukaiyama-type C-glycosidation and a macrolactonization. A total, stereoselective synthesis of the cytotoxic macroli...

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Veröffentlicht in:Tetrahedron letters 2009-07, Vol.50 (27), p.3783-3785
Hauptverfasser: Díaz-Oltra, Santiago, Angulo-Pachón, César A., Kneeteman, María N., Murga, Juan, Carda, Miguel, Marco, J. Alberto
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Sprache:eng
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Zusammenfassung:A stereoselective synthesis of the cytotoxic macrolide aspergillide B has been performed. The three key fragments A, B and C were connected with the aid of a cross metathesis (CRM), a Mukaiyama-type C-glycosidation and a macrolactonization. A total, stereoselective synthesis of the cytotoxic macrolide aspergillide B has been performed. A cross metathesis and a C-glycosidation via a Mukaiyama-type aldol reaction were key features of the synthesis. The macrocyclic lactone ring was created by means of the Yamaguchi procedure.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.04.026