Synthesis of the benzo[b]fluorene core of the kinamycins by arylalkyne-allene and arylalkyne-alkyne cycloadditions

被引：37

作者：

González-Cantalapiedra, E

de Frutos, O

Atienza, C

Mateo, C

Echavarren, AM

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

[2] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 06期

关键词：

quinones; cycloadditions; alkynes; allenes; natural products;

D O I：

10.1002/ejoc.200500926

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arylalkyne-allene and arylalkyne-alkyne cycloadditions yields benzo[a]fluorenones, which are related to the tetracyclic core of the kinamycins. In the arylalkyne-alkyne cycloadditions, we found a rearrangement that produces benzo[a]fluorenones, in addition to the expected benzo[b]fluorenones. This rearrangement could be suppressed in the presence of phenol, which allowed the synthesis of 4,9-dimethoxy-2-methyl-1 1H-benzo[b]fluoren-11-one in excellent yield. (c) Wiley-VCH Verlag GmbH & Co.

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页码：1430 / 1443

页数：14

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