(+)-螺拉嗪甲醚的实用全合成。

A practical total synthesis of (+)-spirolaxine methyl ether.

机构信息

Division of Organic Chemistry, Discovery Laboratory, Indian Institute of Chemical Technology, Hyderabad, India.

出版信息

J Org Chem. 2010 Dec 3;75(23):8307-10. doi: 10.1021/jo1016647. Epub 2010 Nov 8.

Abstract

An efficient and practical total synthesis of (+)-spirolaxine methyl ether is described. The phthalide-aldehyde 3 has been prepared via the Diels-Alder reaction between 1,4-unconjugated diene 5 and a long-chain acetylenic dienophile 6. The carbon framework of spiroketal sulfone 4 has been constructed from monobenzyl protected 1,5-pentanediol and the stereochemistry in both the phthalide portion and the spiroketal portion has been established by the Sharpless asymmetric epoxidation.

摘要

描述了 (+)-螺拉嗪甲醚的一种高效实用的全合成方法。通过 1,4-非共轭二烯 5 和长链炔二烯 6 之间的 Diels-Alder 反应制备了邻苯二甲酸醛 3。螺缩酮砜 4 的碳骨架是由单苄基保护的 1,5-戊二醇构建的，并且通过 Sharpless 不对称环氧化反应确定了邻苯二甲酸部分和螺缩酮部分的立体化学。