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Synthesis of Tricyclic Marine Alkaloids, Cylindricines, Lepadiformines, Fasicularin, and Polycitorols: A Recent Update
Synthesis ( IF 2.2 ) Pub Date : 2017-12-14 , DOI: 10.1055/s-0036-1589521
Shunsuke Chiba , Atsushi Kaga

Abstract

Cylindricines, lepadiformines, and fasicularin are tricyclic marine alkaloids bearing perhydropyrrolo- and pyrido[2,1-j] frameworks having divergent chemical functionalities. They have been isolated from marine tunicates over the last two decades and found to have a range of cytotoxicity such as DNA-alkylating ability. Recently, polycitorols have emerged as a new member of this alkaloid family. Their unique structural features and biological activities have intrigued many researchers and challenged them in their synthesis. This review describes recent syntheses of the tricyclic alkaloids based on key synthetic approaches.

1 Introduction

2 Total and Formal Syntheses

2.1 Overview of Synthetic Strategies

2.2 Azaspirocycle (BC Ring) Approaches

2.3 Indolizidine (AC Ring) Approaches

2.4 Azadecalin (AB Ring) Approaches

2.5 Tandem Cyclization Approaches

3 Summary and Future Perspective

Cylindricines, lepadiformines, and fasicularin are tricyclic marine alkaloids bearing perhydropyrrolo- and pyrido[2,1-j] frameworks having divergent chemical functionalities. They have been isolated from marine tunicates over the last two decades and found to have a range of cytotoxicity such as DNA-alkylating ability. Recently, polycitorols have emerged as a new member of this alkaloid family. Their unique structural features and biological activities have intrigued many researchers and challenged them in their synthesis. This review describes recent syntheses of the tricyclic alkaloids based on key synthetic approaches.

1 Introduction

2 Total and Formal Syntheses

2.1 Overview of Synthetic Strategies

2.2 Azaspirocycle (BC Ring) Approaches

2.3 Indolizidine (AC Ring) Approaches

2.4 Azadecalin (AB Ring) Approaches

2.5 Tandem Cyclization Approaches

3 Summary and Future Perspective



中文翻译:

三环海洋生物碱,cylindricines,lepadiformines,fasicularin和polycitorolols的合成:最近的更新。

摘要

圆柱状蛋白,lepadiformines和fasicularin是带有全氢吡咯并吡咯并[2,1- j ]骨架的三环海洋生物碱,具有不同的化学功能。在过去的二十年中,它们已从海洋被膜中分离出来,并发现具有一定的细胞毒性,例如DNA烷基化能力。近来,聚瓜酚已经成为该生物碱家族的新成员。它们独特的结构特征和生物学活性吸引了许多研究人员,并在合成过程中提出了挑战。这篇综述描述了基于关键合成方法的三环生物碱的最新合成方法。

1引言

2全面综合和形式综合

2.1综合策略概述

2.2 Azaspirocycle(BC环)方法

2.3吲哚并咪唑(AC环)方法

2.4 Azadecalin(AB环)方法

2.5串联环化方法

3总结与未来展望

圆柱状蛋白,lepadiformines和fasicularin是带有全氢吡咯并吡咯并[2,1- j ]骨架的三环海洋生物碱,具有不同的化学功能。在过去的二十年中,它们已从海洋被膜中分离出来,并发现具有一定的细胞毒性,例如DNA烷基化能力。近来,聚瓜酚已经成为该生物碱家族的新成员。它们独特的结构特征和生物学活性吸引了许多研究人员,并在合成过程中提出了挑战。这篇综述描述了基于关键合成方法的三环生物碱的最新合成方法。

1引言

2全面综合和形式综合

2.1综合策略概述

2.2 Azaspirocycle(BC环)方法

2.3吲哚并咪唑(AC环)方法

2.4 Azadecalin(AB环)方法

2.5串联环化方法

3总结与未来展望

更新日期:2017-12-14
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