DIELS-ALDER CYCLO-ADDITION OF JUGLONE DERIVATIVES .2. REGIOSPECIFICITY OF REACTIONS LEADING TO TETRACYCLIC ANTHRACYCLINONE SYSTEMS

被引：28

作者：

BOECKMAN, RK

DELTON, MH

DOLAK, TM

WATANABE, T

GLICK, MD

机构：

[1] Department of Chemistry, Wayne State University, Detroit, Michigan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 24期

关键词：

D O I：

10.1021/jo01338a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regiospecificity of the reaction of several juglone derivatives with two complex dienes derived from bicyclic dimethoxycyclobutenes has been examined as part of a series of model studies leading toward the synthesis of the anthracyclinone antibiotics adriamycin and daunorubicin. In general, regiospecificity appears governed primarily by diene polarization factors. The structural assignments have been confirmed by a single-crystal X-ray analysis of one of the tetracyclic adducts from juglone methyl ether and related by chemical interconversion. © 1979, American Chemical Society. All rights reserved.

引用

页码：4396 / 4402

页数：7

共 18 条

[1] SECONDARY ORBITAL INTERACTIONS DETERMINING REGIOSELECTIVITY IN LEWIS ACID-CATALYZED DIELS-ALDER REACTION .2. [J].