（±）-阿朴啡型单萜吲哚生物碱（±）-阿朴宁的短合成路线。

Short Synthesis of the Monoterpene Indole Alkaloid (±)-Arbornamine.

机构信息

State Key Laboratory of Phytochemistry and Plant Resources in West China , Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201 , China.

University of Chinese Academy of Sciences , Beijing 100049 , China.

出版信息

J Org Chem. 2018 Apr 20;83(8):4867-4870. doi: 10.1021/acs.joc.8b00529. Epub 2018 Apr 5.

DOI:10.1021/acs.joc.8b00529

PMID:29589936

Abstract

The first total synthesis of the monoterpene indole alkaloid (±)-arbornamine (1) has been completed, which proceeds in only 6 steps and 31% overall yield from three readily available, known compounds. The synthesis features a cascade involving a Pictet-Spengler cyclization/intramolecular ammonolysis to create the tetracyclic core of arbornamine (1) in a single chemical operation. The subsequent elaboration of 5 into 1 was effected by a key reductive Heck reaction and global reduction.

摘要

首次完成了单萜吲哚生物碱（±）-阿罗因的全合成（1），仅通过 6 步反应，以 3 个易得的已知化合物为原料，以 31%的总收率即可完成。该合成方法具有级联反应特征，涉及到Pictet-Spengler 环化/分子内氨解反应，可在单次化学反应中构建阿罗因（1）的四环核心。随后通过关键的还原 Heck 反应和全局还原反应，将 5 转化为 1。