[4 + 2]-Annulations of Chiral Organosilanes:  Application to the Total Synthesis of Leucascandrolide A

Complete details of an asymmetric synthesis of leucascandrolide A (1) are described. The synthesis highlights the use of two diastereoselective [4 + 2]-annulations for the assembly of the functionalized bispyranyl macrolide 3. An efficient assembly and union of the oxazole-containing side chain 4 wi...

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Veröffentlicht in:Journal of organic chemistry 2007-01, Vol.72 (1), p.2-24
Hauptverfasser: Su, Qibin, Dakin, Les A, Panek, James S
Format: Artikel
Sprache:eng
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Zusammenfassung:Complete details of an asymmetric synthesis of leucascandrolide A (1) are described. The synthesis highlights the use of two diastereoselective [4 + 2]-annulations for the assembly of the functionalized bispyranyl macrolide 3. An efficient assembly and union of the oxazole-containing side chain 4 with macrolide 3 was carried out using a Mitsunobu reaction. A convergent route to the oxazole side chain was developed using a Sonogashira cross-coupling between 2-trifloyloxazole 16 and alkyne 17, which allowed for the installation of the C9‘−C10‘ (Z)-olefin.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0610412