Synthesis of (+/-)-coerulescine and a formal synthesis of (+/-)-horsfiline

被引：69

作者：

Chang, MY ^{[1
]}

Pai, CL

Kung, YH

机构：

[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan

[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 49期

关键词：

coerulescine; horsfiline; 4-hydroxypiperidine; Lewis acid catalyzed rearrangement; 3-formyl-3-phenylpyrrolidine; 3,4-dihydroxy-4-phenylpiperidine;

D O I：

10.1016/j.tetlet.2005.10.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward synthesis of (+/-)-coerulescine and (+/-)-horsfiline has been established from 3-formyl-3-phenylpyrridine employing 4-hydroxypiperidine as the starting material. There are two remarkable steps for the synthesis of (+/-)-coerulescine and ()-horsfiline. One is the rapid access to produce 3-formyl-3-phenylpyrrolidine by Lewis acid-catalyzed rearrangement of 3,4-dihydroxy-4-phenylpiperidine. The other key step is an intramolecular electrophilic cyclization from 3-benzylcarbamoyl-3-plienylpyrrolidine to the 3,3-spirocyclic 2-oxindole ring skeleton. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8463 / 8465

页数：3

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