使用炔烃构建模块全合成海鞘胺型生物碱。

Total synthesis of ascididemin-type alkaloids using alkyne building blocks.

作者信息

Yin Hao, Shan Naiyu, Wang Shaozhong, Yao Zhu-Jun

机构信息

State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University , Nanjing 210093, P. R. China.

出版信息

J Org Chem. 2014 Oct 17;79(20):9748-53. doi: 10.1021/jo501927e. Epub 2014 Sep 30.

DOI:10.1021/jo501927e

PMID:25238030

Abstract

A common approach to ascididemin-type alkaloids, including ascididemin, bromoleptoclinidinone, neocalliactine acetate, and 11-hydroxyascididemin, based on a Brønsted acid-promoted tandem annulation has been developed. Alkyne building blocks were first designed and then employed in alkaloid synthesis; these building blocks can be accessed by a Sonogashira coupling reaction on a multigram scale.

摘要

基于布朗斯特酸促进的串联环化反应，已开发出一种用于合成海鞘胺型生物碱（包括海鞘胺、溴化细颈海鞘定酮、新海鞘素乙酸酯和11-羟基海鞘胺）的通用方法。首先设计了炔烃构建块，然后将其用于生物碱合成；这些构建块可以通过多克规模的Sonogashira偶联反应获得。