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An Efficient Synthesis of a (−)‐Physostigmine's Library for Identifying Potential Anti‐ Alzheimer 's Agents
Author(s) -
Wu Yi,
Wang Fusheng,
Song Hao,
Qin Yong
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100020
Subject(s) - chemistry , cycloaddition , physostigmine , azide , propargyl , combinatorial chemistry , natural product , organic chemistry , stereochemistry , catalysis , acetylcholine , medicine , endocrinology
An efficient route for the synthesis of (−)‐physostigmine analogs 1a – 1g and 2a – 2k is described. Analogs 1a – 1g were synthesized via copper(I)‐catalyzed cycloaddition between the optically pure azide 10 and a variety of alkynes. Similarly, analogs 2a – 2k were prepared through ‘three‐component Huisgen cycloaddition’ using various amines, propargyl bromine, and 10 in H 2 O. Facile preparation of 10 via MacMillan 's organocatalysis has made it possible to generate a great diversity of natural product‐like compounds that can be screened for anti‐ Alzheimer 's effects.