350245-33-9Relevant 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.
Synthesis of the isocoumarin portion of the rubromycins
Waters, Stephen P.,Kozlowski, Marisa C.
, p. 3567 - 3570 (2007/10/03)
A synthesis of the isocoumarin found in the rubromycin class of natural products is reported. The isocoumarin ring system is formed via Heck coupling of a pyruvate synthon with a terephthalic acid derivative followed by an intramolecular acid-catalyzed cyclization. The requisite terephthalic acid precursor is generated by carboxylation of catechol and then desymmetrization of the aromatic ring by halogenation. The isocoumarin derivative that has been produced is an appropriate precursor for the synthesis of γ-rubromycin, purpuromycin, and heliquinomycin.
