1255790-40-9Relevant academic research and scientific papers
Studies toward the syntheses of pluramycin natural products. the first total synthesis of isokidamycin
O'Keefe, B. Michael,Mans, Douglas M.,Kaelin Jr., David E.,Martin, Stephen F.
, p. 6524 - 6538 (2011/09/20)
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 tether to link the reactive naphthyne and the glycosyl furan, rendering the cycloaddition intramolecular. The benzopyranone moiety of 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 O→C-glycoside rearrangement that produced the β-anomer. Subsequent refunctionalizations then led to isokidamycin.
Total synthesis of isokidamycin
O'Keefe, B. Michael,Mans, Douglas M.,Kaelin Jr., David E.,Martin, Stephen F.
scheme or table, p. 15528 - 15530 (2011/01/12)
The synthesis of isokidamycin, which represents the first total synthesis of a bis-C-aryl glycoside natural product in the pluramycin family, has been completed. The synthesis features the use of a silicon tether as a disposable regiocontrol element in an intramolecular Diels-Alder reaction between a substituted naphthyne and a glycosyl furan and a subsequent O→C-glycoside rearrangement.
