Tetrahedron

Syntheses of differentially protected isocoumarins

AN Lowell, PD Wall, SP Waters, MC Kozlowski

Index: Lowell, Andrew N.; Wall, Philip D.; Waters, Stephen P.; Kozlowski, Marisa C. Tetrahedron, 2010 , vol. 66, # 30 p. 5573 - 5582

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Citation Number: 14

Abstract

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 ...

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