利用串联克莱森/狄尔斯-阿尔德/克莱森重排反应对福布斯酮和去氧莫雷林进行仿生全合成。
Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels--Alder/Claisen rearrangement.
作者信息
Tisdale Eric J, Slobodov Irina, Theodorakis Emmanuel A
机构信息
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla 92093-0358, USA.
出版信息
Org Biomol Chem. 2003 Dec 21;1(24):4418-22. doi: 10.1039/b311833a.
A concise synthesis of forbesione (1) and desoxymorellin (3) is presented. Central to the strategy is a biomimetic Claisen/Diels-Alder/Claisen reaction cascade that proceeds in a regioselective manner and produces the desired scaffold exclusively. The observed regioselectivity and product distribution of the Claisen/Diels-Alder/Claisen reaction are attributed to the electronic effects of the xanthone oxygen (O10), the C9 carbonyl group and the nature of the C1 functionality.
本文介绍了福贝西酮（1）和去氧莫雷林（3）的简洁合成方法。该策略的核心是一个仿生克莱森/狄尔斯-阿尔德/克莱森反应级联，该反应以区域选择性方式进行，仅生成所需的骨架。克莱森/狄尔斯-阿尔德/克莱森反应观察到的区域选择性和产物分布归因于呫吨酮氧（O10）、C9羰基的电子效应以及C1官能团的性质。
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