Studies toward the syntheses of pluramycin natural products. The first total synthesis of isokidamycin

BM O'Keefe, DM Mans, DE Kaelin, SF Martin

Index: O'Keefe, B. Michael; Mans, Douglas M.; Kaelin Jr., David E.; Martin, Stephen F. Tetrahedron, 2011 , vol. 67, # 35 p. 6524 - 6538

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Citation Number: 8

Abstract

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 efficient Diels–Alder reaction between a substituted naphthyne and a glycosylated furan to form the anthracene core bearing a pendent angolosamine C-glycoside. The regiochemical outcome of the Diels–Alder reaction was controlled by employing a disposable silicon ...