Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families
Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families
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DOI：
10.1021/ja047874w
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发表时间：
2004-06-23
影响因子：
15
通讯作者：
Richter, JM
中科院分区：
文献类型：
--
作者：
Baran, PS;Richter, JM
本发明描述了吲哚和羰基化合物（酮、酰胺、酯）直接结合的方法。利用这种新方法，从香芹酮和吲哚出发，实现了一个短的、对映选择性的、克级的、不含保护基的非舍吲哚和hapalindole吲哚生物碱家族的合成。报道了（+）-hapalindole Q和（−）-12-epi-fischerindole U异硫氰酸酯的全合成。后者的天然产物的绝对立体化学也已确定。
The invention of a method for the direct union of indoles and carbonyl compounds (ketones, amides, esters) is described. Using this new method, a short, enantioselective, gram-scale and protecting group-free synthetic entry to the fischerindole and hapalindole indole alkaloid family has been achieved from carvone and indole. Total syntheses of (+)-hapalindole Q and (−)-12-epi-fischerindole U isothiocyanate are reported. The absolute stereochemistry of the latter natural product has also been determined.