Investigation of a Convergent Route to Purpuromycin: Benzofuran Formation vs Spiroketalization
2006; American Chemical Society; Volume: 8; Issue: 15 Linguagem: Inglês
10.1021/ol061112j
ISSN1523-7060
AutoresStephen P. Waters, Michael W. Fennie, Marisa C. Kozlowski,
Tópico(s)Organic Chemistry Cycloaddition Reactions
ResumoA mild and efficient [3+2] nitrile oxide/olefin cycloaddition allows coupling of the highly functionalized naphthalene and isocoumarin hemispheres of purpuromycin. A rationale of the inability of advanced keto alcohols to spirocyclize is presented based upon a systematic examination of the electronic factors present in these systems and suggests that the biosynthesis of purpuromycin does not proceed through open-chain intermediates.
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