908338-90-9Relevant academic research and scientific papers
Syntheses of differentially protected isocoumarins
Lowell, Andrew N.,Wall, Philip D.,Waters, Stephen P.,Kozlowski, Marisa C.
experimental part, p. 5573 - 5582 (2010/10/01)
Syntheses of an isocoumarin subunit suitable for the completion of purpuromycin are outlined. Specifically, work targeting an orthogonally protected isocoumarin (eventually 12% yield over 12 steps) and an improved synthesis of a symmetrically protected isocoumarin (18% over 10 steps) are described. A new modification for selective catechol protection as mediated by potassium bicarbonate is also presented along with insights into oxidative and reductive functionalization of isocoumarins.
Investigation of a convergent route to purpuromycin: Benzofuran formation vs spiroketalization
Waters, Stephen P.,Fennie, Michael W.,Kozlowski, Marisa C.
, p. 3243 - 3246 (2007/10/03)
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 u
