在四环苦木素中间体的汇聚式立体选择性合成中，麦氏酸衍生的硫酮亲双烯体。
Meldrum's acid-derived thione dienophile in a convergent and stereoselective synthesis of a tetracyclic quassinoid intermediate.
作者信息
Perreault Stéphane, Spino Claude
机构信息
Département de Chimie, Université de Sherbrooke, Sherbrooke, Québec J1K 2R1, Canada.
出版信息
Org Lett. 2006 Sep 28;8(20):4385-8. doi: 10.1021/ol060892t.
PMID:16986906
Abstract
An advanced intermediate toward anti-cancer quassinoids has been synthesized using a quadruple diene-transmissive [4+2]-cycloaddition strategy. High convergence is achieved thanks to a regio- and stereoselective hetero-Diels-Alder reaction using a thione. The relative stereochemistry of the final Diels-Alder adduct was controlled by tethered substituents introduced via a highly syn- and gamma-selective vinylogous Mukaiyama aldol.
摘要
采用四重双烯传递型[4+2]环加成策略合成了一种抗癌苦木素类化合物的高级中间体。由于使用硫酮进行区域和立体选择性杂Diels-Alder反应，实现了高收敛性。最终Diels-Alder加合物的相对立体化学由通过高度顺式和γ选择性乙烯基Mukaiyama羟醛反应引入的连接取代基控制。
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