APPROACHES TO THE REGIOSPECIFIC SYNTHESIS OF ANTHRACYCLINE ANTIBIOTICS-1ALPHA

被引：12

作者：

BALDWIN, JE ^{[1
]}

RAJECKAS, AJ ^{[1
]}

机构：

[1] MIT, DEPT CHEM, CAMBRIDGE, MA 02139 USA

来源：

TETRAHEDRON | 1982年 / 38卷 / 20期

关键词：

D O I：

10.1016/0040-4020(82)80196-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetic approaches to anthracycline antibiotics, clinically useful for treatment of human cancers, were studied through Claisen rearrangements on 1-methallyloxy-5-methoxyanthraquinine (9), which required reducing conditions to proceed through a hydroquinone intermediate in situ. 1-(2''-Methylene-4''-pentenoxy)-5-methoxyanthraquinone (13) underwent a similar reductive rearrangement but also produced a spiro compound 16 as a result of an ene reaction between the phenol and side chain double bond. 1-Hydroxy-2-methallyl-5-methoxyanthraquinone (11) could not be oxidized to quinizarin 17. 1-Hydroxy-2-methallyl-5,9,10-trimethoxyanthracene (21) was oxidatively coupled to the dimer at C-2. Dimer 23 reacted with diazomethane to form a 1,3-dipolar adduct 24.

引用

页码：3079 / 3084

页数：6

共 46 条

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