Studies Toward the Syntheses of Pluramycin Natural Products. The First Total Synthesis of Isokidamycin.
Tetrahedron
; 67(35): 6524-6538, 2011 Sep 02.
Article
em En
| MEDLINE
| ID: mdl-21804649
We report the first total synthesis of the complex C-aryl glycoside isokidamycin, the epimer of the naturally-occurring pluramycin antibiotic kidamycin. The synthesis features a highly efficientDiels-Alder reaction between a substituted naphthyne and a glycosylatedfuran to form the anthracene core bearing a pendant angolosamine C-glycoside. The regiochemical outcome of the Diels-Alder reaction was controlled by employing a disposable silicon-tether to link the reactive napthyne and the glycosyl furan, rendering the cycloaddition intramolecular. The benzopyranone moietyof the aromatic nucleus was appended by cyclization of a functionalized vinylogous amide onto an advanced anthrol intermediate. The vancosamine amino glycoside was introduced by an OâC-glycoside rearrangement that produced the ß-anomer. Subsequent refunctionalizations then led to isokidamycin.
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MEDLINE
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2011
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Article