The first stereoselective total synthesis of a potent antitumor alkaloid, discorhabdin A (1), which is a unique sulfur-containing pyrroloiminoquinone alkaloid, is described. The key step in the stereocontrolled total synthesis of 1 involves both a diastereoselective oxidative spirocyclization using a hypervalent iodine(III) reagent and an efficient construction of the labile and highly strained N,S-acetal skeleton. These methodologies provide a breakthrough in the total syntheses of these promising new antitumor agents, discorhabdins and their analogues, which should serve as valuable probes for structure-activity studies.
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NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA
Dijoux, MG
Gamble, WR
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NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA
Gamble, WR
Hallock, YF
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NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA
Hallock, YF
Cardellina, JH
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NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA
Cardellina, JH
van Soest, R
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NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA
van Soest, R
Boyd, MR
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NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA
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NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA
Dijoux, MG
Gamble, WR
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NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA
Gamble, WR
Hallock, YF
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NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA
Hallock, YF
Cardellina, JH
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NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA
Cardellina, JH
van Soest, R
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NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA
van Soest, R
Boyd, MR
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机构:
NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USANCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Lab Drug Discovery Res & Dev,Dev Therapeut Progra, Frederick, MD 21702 USA