Studies on the Syntheses of Benzoquinone Ansamycin Antibiotics. Syntheses of the C(5)−C(15) Subunits of Macbecin I, Geldanamycin, and Herbimycin A

Studies on the Syntheses of Benzoquinone Ansamycin Antibiotics. Syntheses of the C(5)−C(15) Subunits of Macbecin I, Geldanamycin, and Herbimycin A

A general and convergent route to the C(5)−C(15) subunits of the benzoquinone ansamycin antibiotics macbecin I, geldanamycin, and herbimycin A is described. Each subunit is prepared by the stepwise coupling of differentially functionalized aldehydes with a pentenyl dianion equivalent derived from di...

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Veröffentlicht in:Organic letters 2006-05, Vol.8 (11), p.2409-2412
Hauptverfasser: Belardi, Justin K, Micalizio, Glenn C
Format: Artikel
Sprache:eng
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Zusammenfassung:A general and convergent route to the C(5)−C(15) subunits of the benzoquinone ansamycin antibiotics macbecin I, geldanamycin, and herbimycin A is described. Each subunit is prepared by the stepwise coupling of differentially functionalized aldehydes with a pentenyl dianion equivalent derived from diastereoselective pentynylation and regioselective reductive coupling.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0607995