Total Synthesis of the β-Catenin Inhibitor, (-)-Agelastatin A: A Second-Generation Approach Based on Radical Aminobromination

被引：34

作者：

Yoshimitsu, Takehiko ^{[1
]}

Ino, Tatsunori ^{[1
]}

Futamura, Naoyuki ^{[1
]}

Kamon, Takuma ^{[1
]}

Tanaka, Tetsuaki ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 15期

关键词：

SPONGE AGELAS-DENDROMORPHA; ALKYNYLIODONIUM SALTS; ORGANIC-SYNTHESIS; REARRANGEMENT;

D O I：

10.1021/ol9012684

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The second-generation approach to (-)-agelastatin A has been established. The present strategy features the FeBr2-mediated radical cyclization of 2-cyclopentenyloxycarbonyl azide that allows for the stereoselective installation of a cis-vicinal aminobromo functionality suitable for producing the BCD-ring system of agelastatin A. The aminobromination method streamlines access to oxazolidinone, a key intermediate in the previously reported synthesis, thereby culminating in the new total synthesis of (-)-agelastatin A.

引用

页码：3402 / 3405

页数：4

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