Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 128, Issue 38, Pages 12562-12573Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja0642616
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Funding
- NIGMS NIH HHS [GM 37861, R01 GM037681-19] Funding Source: Medline
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The putative reductive activation chemistry of the diazoparaquinone antibiotics was modeled with Bu3Sn-H and prekinamycin dimethyl ether along with prekinamycin itself. Reaction in various combinations of aromatic solvents, with and without the nucleophile benzylmercaptan present, led to isolation of both radical-trapping arene adducts and nucleophilic capture benzyl thioether products. On the basis of these product distribution studies, the intermediacies of, first, a cyclopentenyl radical and, next, an orthoquinonemethide electrophile are postulated.
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