Investigation of a convergent route to purpuromycin: benzofuran formation vs spiroketalization.
作者信息
Waters Stephen P, Fennie Michael W, Kozlowski Marisa C
机构信息
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
出版信息
Org Lett. 2006 Jul 20;8(15):3243-6. doi: 10.1021/ol061112j.
PMID:16836376
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.
摘要
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