Total Synthesis of (−)-Kendomycin

Total Synthesis of (−)-Kendomycin

An enantioselective synthesis of (−)-kendomycin is described and is based on the application of the organosilane-based [4 + 2]-annulation strategy for the assembly of the C1a−C10 fragment. An underutilized samarium(II) iodide-assisted cyclization (intramolecular Barbier-type reaction) is employed to...

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Veröffentlicht in:Organic letters 2008-09, Vol.10 (17), p.3813-3816
Hauptverfasser: Lowe, Jason T, Panek, James S
Format: Artikel
Sprache:eng
Schlagworte:
Cyclization
Iodides - chemistry
Rifabutin - analogs & derivatives
Rifabutin - chemical synthesis
Samarium - chemistry
Stereoisomerism
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Zusammenfassung:An enantioselective synthesis of (−)-kendomycin is described and is based on the application of the organosilane-based [4 + 2]-annulation strategy for the assembly of the C1a−C10 fragment. An underutilized samarium(II) iodide-assisted cyclization (intramolecular Barbier-type reaction) is employed to afford the protected macrocycle.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801499s