Abstract
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.
Original language | English (US) |
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Pages (from-to) | 12562-12573 |
Number of pages | 12 |
Journal | Journal of the American Chemical Society |
Volume | 128 |
Issue number | 38 |
DOIs | |
State | Published - Sep 27 2006 |
All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry