Construction of the cyclopenta[1,3]cyclopropa[1,2-b]naphthalene system in a one-pot domino reactions

被引：0
|
作者：
Krohn, K [1 ]
Freund, C [1 ]
Flörke, U [1 ]
机构：
[1] Univ Gesamthsch Paderborn, Fachbereich Chem & Chem Tech, D-33098 Paderborn, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 1998卷 / 12期
关键词：
domino reactions; spirocyclization; Michael additions; beta-dicarbonyl compounds; nucleophilic substitution;
D O I：
10.1002/(SICI)1099-0690(199812)1998:12<2713::AID-EJOC2713>3.0.CO;2-G
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Base treatment of the angucycline oligoketide precursor 6 unexpectedly afforded the spirocyclization product 7. An additional step in the domino cyclization process was observed starting from the quinoid bromo diketone 3b to yield stereospecifically the condensed tetracycle 8 with the benzo-annelated skeleton of the cubebol-type sesquiterpenes. The structure of 8 was confirmed by X-ray structure analysis. Further extension of the domino sequence by reaction of the dibromide 10 with acetonedicarboxylic eater II gave the cyclization/condensation products 12, 13, or 14, depending on the reaction conditions.
引用
收藏
页码：2713 / 2718
页数：6
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