A Direct and Efficient Total Synthesis of the Tubulin-Binding Agents Ceratamine A and B; Use of IBX for a Remarkable Heterocycle Dehydrogenation

被引：26

作者：

Coleman, Robert S. ^{[1
]}

Campbell, Erica L. ^{[1
]}

Carper, Daniel J. ^{[1
]}

机构：

[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 10期

关键词：

SPONGE ALKALOID-CERATAMINE; ANTIMITOTIC AGENTS; PSEUDOCERATINA SP; ANALOGS; CONVENIENT; REDUCTION; OXIDATION; ALDEHYDES; KETONES; AMINES;

D O I：

10.1021/ol900709n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the tubulin-binding agents ceratamine A and B is reported, along with des-methyl analogs, via a synthetic route that is high-yielding and operationally efficient. The synthetic route involved a Beckmann rearrangement to form an azepine ring precursor, a Knoevenagel condensation to install the benzylic side chain, and an effective imidazole annulation onto an alpha-aminoketone precursor with a protected S-methylisothiourea. Final dehydrogenation proved remarkably facile using IBX.

引用

页码：2133 / 2136

页数：4

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