用于全合成（±）-拉帕替尼B的酸催化氮杂狄尔斯-阿尔德反应

Acid-catalyzed aza-Diels-Alder reactions for the total synthesis of (+/-)-lapatin B.

作者信息

Leca Dominique, Gaggini Francesca, Cassayre Jérôme, Loiseleur Olivier, Pieniazek Susan N, Luft Jennifer A R, Houk K N

机构信息

SYNGENTA Crop Protection AG, Research Chemistry, CH-4002 Basel, Switzerland.

出版信息

J Org Chem. 2007 May 25;72(11):4284-7. doi: 10.1021/jo0705162. Epub 2007 May 5.

DOI:10.1021/jo0705162

PMID:17480097

Abstract

A 5-step total synthesis of microfungal alkaloid (+/-)-lapatin B has been accomplished via a key 2-aza-Diels-Alder reaction. Brønsted acids catalyze the cycloaddition step and provide improved exo selectivity. This synthetic route has been applied to the construction of related spiro-quinazoline structures.

摘要

通过关键的2-氮杂-狄尔斯-阿尔德反应完成了微真菌生物碱（±）-拉帕替尼B的五步全合成。布朗斯特酸催化环加成步骤并提高了外型选择性。该合成路线已应用于相关螺喹唑啉结构的构建。