Synthetic studies towards dendridine A: synthesis of hemi-dendridine A acetate by Fischer indolization

被引：6

作者：

Boyd, Emily M. ^{[1
]}

Sperry, Jonathan ^{[1
]}

机构：

[1] Univ Auckland, Sch Chem Sci, Auckland 1, New Zealand

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 28期

关键词：

Dendridine A; Bisindole; Abnormal Fischer indolization; Alkaloid; Tryptamine; 5,6-DIHYDROXYINDOLE-2-CARBOXYLIC ACID; 7-OXYGENATED INDOLES; FACILE SYNTHESIS; EUDISTOMIDIN-A; N-ALLYLAMIDES; 1ST SYNTHESIS; MELATONIN; MASTIGOPHORENES; 1-AMINOINDOLES; ISOMERIZATION;

D O I：

10.1016/j.tetlet.2012.05.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short synthesis of hemi-dendridine A acetate has been accomplished. The synthesis is based on a modified Fischer indolization that represents a rare example of the single-step synthesis of a 7-oxytryptamine from an ortho-oxygenated phenylhydrazine. The synthetic route required developing an efficient synthesis of N-acetyl-2-pyrroline, the key coupling partner for the modified Fischer indolization. Some interesting chemistry associated with the abnormal Fischer indolization has been uncovered, whereby two molecules of the phenylhydrazine substrate combined along the abnormal reaction pathway, affording an unusual N-phenylindoleamine product. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3623 / 3626

页数：4

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