SELENIUM DIOXIDE OXIDATIONS IN THE INDOLE AREA - SYNTHESIS OF BETA-CARBOLINE ALKALOIDS
SELENIUM DIOXIDE OXIDATIONS IN THE INDOLE AREA - SYNTHESIS OF BETA-CARBOLINE ALKALOIDS
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DOI：
10.1021/ja00342a045
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发表时间：
1983-01-01
影响因子：
15
通讯作者：
COOK, JM
中科院分区：
文献类型：
--
作者：
CAIN, M;CAMPOS, O;COOK, JM
A number of different piperidoindole systems have been subjected to oxidation with selenium dioxide. The bonding between the indole and piperidine unit has been varied to provide different systems, the oxidation of which has led to formation of either 2-acyl-or 3-acylindoles or fully aromatic/3-carbolines, depending on the substrate chosen. The patternof reactivity observed was in complete agreement with the ene mechanism proposed for selenium dioxide oxidations, and this can be employed to predict the regiochemistry of the oxidation. Use of this technology has resulted in a two-step synthesis of the indole alkaloid canthin-6-one (30a).Selenium dioxide has been shown to be an effective reagent for regioselective incorporationof oxygen functionality at allylic positions; 1 in a previous communication2 we reported use of this technology for preparation of 3-acylindoles. 3 Moreover, the reagent has been employed in our laboratory to prepare 0-car-bolines, a class of compounds that have been shown tobind tightly to the benzodiazepine receptorin vitro and were found to be benzodiazepine receptor antagonists in vivo. 4 567" 8
