Syntheses of differentially protected isocoumarins

被引：15

作者：

Lowell, Andrew N. ^{[1
]}

Wall, Philip D. ^{[1
]}

Waters, Stephen P. ^{[1
]}

Kozlowski, Marisa C. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

TETRAHEDRON | 2010年 / 66卷 / 30期

关键词：

Isocoumarin; Rubromycin; Orthogonal protection; Selective oxidation; PALLADIUM-CATALYZED COUPLINGS; CONVERGENT ROUTE; RUBROMYCINS; SPIROKETALIZATION; PURPUROMYCIN; DERIVATIVES; PHOMAZARIN; VINYLATION; PRECURSOR; EFFICIENT;

D O I：

10.1016/j.tet.2010.05.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：5573 / 5582

页数：10

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