串联金催化脱水环化/狄尔斯-阿尔德反应：简便合成吲哚咔唑生物碱
Tandem gold-catalyzed dehydrative cyclization/diels-alder reactions: facile access to indolocarbazole alkaloids.
作者信息
Borrero Nicholas V, DeRatt Lindsey G, Ferreira Barbosa Lais, Abboud Khalil A, Aponick Aaron
机构信息
Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, Florida 32611, United States.
出版信息
Org Lett. 2015 Apr 3;17(7):1754-7. doi: 10.1021/acs.orglett.5b00528. Epub 2015 Mar 23.
A gold-catalyzed synthesis of cyclic 2-oxodienes from readily prepared propargyl alcohols and the subsequent Diels-Alder reaction are reported. The dehydrative cyclization reactions proceeded smoothly, and the dienes formed in situ were demonstrated to undergo cycloaddition with a variety of dienophiles. This method offers a new strategy for the synthesis of indolocarbazole alkaloids, whereby the convergent synthetic design allows for differentiation between the indole nitrogens.
报道了一种由容易制备的炔丙醇经金催化合成环状2-氧代二烯以及随后的狄尔斯-阿尔德反应。脱水环化反应顺利进行，原位生成的二烯被证明能与多种亲双烯体发生环加成反应。该方法为吲哚咔唑生物碱的合成提供了一种新策略，其中汇聚式合成设计能够区分吲哚氮原子。
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