[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 |
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Hauptverfasser: | , , |
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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo0610412 |