SYNTHESIS OF (+/-)-FREDERICAMYCIN-A

被引：69

作者：

WENDT, JA ^{[1
]}

GAUVREAU, PJ ^{[1
]}

BACH, RD ^{[1
]}

机构：

[1] WAYNE STATE UNIV,DEPT CHEM,DETROIT,MI 48202

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 22期

关键词：

D O I：

10.1021/ja00101a013

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of (+/-)-fredericamycin A (1) is reported with full experimental detail. Preparations of building blocks for the upper (2) and lower (3) units of 1 are described. The union of 2 and 3 by a two-step 1,4-dipolar cycloaddition and the elaboration of the resulting product (19) into 1 are presented. The spiro 1,3-dione center in 1 was introduced utilizing a mild mercury-mediated pinacol rearrangement involving a 1,2-carbonyl migration. The reaction of benzylic cuprate anions ortho to aromatic esters has been shown to produce isochromarins in good yield. These isochromarins afford the biologically relevant isoquinolones upon treatment with ammonia.

引用

页码：9921 / 9926

页数：6

共 66 条

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[2]

AYYANGAR NR, 1988, SYNTHETIC COMMUN, V18, P633

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