首次合成2,2 - 二甲基 - 7 -（2'-甲基丁 - 3'-烯 - 2'-基）- 2H - 色烯 - 6 - 醇和2 -（3'-甲基丁 - 2'-烯基）- 5 -（2'-甲基丁 - 3'-烯 - 2'-基）- 1,4 - 苯醌，这两种新型的异戊烯基化醌类衍生物来自新西兰褐藻Perithalia capillaris。

First syntheses of 2,2-dimethyl-7-(2'-methylbut-3'-en-2'-yl)-2H-chromen-6-ol and 2-(3'-methylbut-2'-enyl)-5-(2'-methylbut-3'-en-2'-yl)-1,4-benzoquinone, novel prenylated quinone derivatives from the New Zealand brown alga Perithalia capillaris.

作者信息

Coombes Catherine L, Moody Christopher J

机构信息

School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.

出版信息

J Org Chem. 2008 Sep 5;73(17):6758-62. doi: 10.1021/jo801057x. Epub 2008 Aug 6.

DOI:10.1021/jo801057x

PMID:18681403

Abstract

The first syntheses of 2,2-dimethyl-7-(2'-methylbut-3'-en-2'-yl)-2H-chromen-6-ol (1) and 2-(3'-methylbut-2'-enyl)-5-(2'-methylbut-3'-en-2'-yl)-1,4-benzoquinone (2), novel prenylated quinone derivatives from the New Zealand brown alga Perithalia capillaris, are reported, in which the key steps are consecutive Claisen rearrangements that proceed with both high chemo- and regioselectivity.

摘要

报道了从新西兰褐藻Perithalia capillaris中首次合成2,2 - 二甲基 - 7 - (2'-甲基丁 - 3'-烯 - 2'-基)-2H - 色烯 - 6 - 醇（1）和2 - (3'-甲基丁 - 2'-烯基)-5 - (2'-甲基丁 - 3'-烯 - 2'-基)-1,4 - 苯醌（2），这两种新型的异戊烯基化醌衍生物的关键步骤是连续的克莱森重排反应，该反应具有高化学选择性和区域选择性。