Mulberry Diels-Alder Adducts: Synthesis of Chalcomoracin and Mulberrofuran C Methyl Ethers
Mulberry Diels-Alder Adducts: Synthesis of Chalcomoracin and Mulberrofuran C Methyl Ethers
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DOI：
10.1021/ol9026705
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发表时间：
2010-04-02
期刊：
影响因子：
5.2
通讯作者：
Rizzacasa, Mark A.
中科院分区：
文献类型：
--
作者：
Gunawan, Christian;Rizzacasa, Mark A.
本文报道了桑葚Diels-Alder加合物查氏菌素（1）和桑树呋喃J（2）的七甲基醚的合成。每种方法的关键步骤都涉及由类异戊二烯取代的酚类化合物衍生的脱氢异戊二烯基苯酚二烯与作为亲二烯体的查尔酮的α，β-不饱和烯烃之间的仿生分子间[4+2]-环加成。Diels-Alder反应成功的关键是2 '-羟基查耳酮中游离苯酚的存在。
The synthesis of each of the heptamethyl ethers of the mulberry Diels-Alder adducts chalcomoracin (1) and mulberrofuran J (2) Is described. The key steps in each approach Involved a biomimetic Intermolecular [4+2]-cycloaddition between a dehydroprenylphenol diene derived from an Isoprenoid-substituted phenolic compound and an alpha,beta-unsaturated alkene of a chalcone as the dienophile. Critical to the success of the Diels-Alder reaction was the presence of the free phenol in the 2'-hydroxychalcone.