S. P. Waters, M. W. Fennie, M. Kozlowski
Jun 30, 2006
Citations
0
Influential Citations
35
Citations
Journal
Organic letters
Abstract
[Structure: see text] A 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.