School of Chemistry, The Bio21 Institute, The University of Melbourne, Victoria 3010, Australia.
Org Lett. 2010 Apr 2;12(7):1388-91. doi: 10.1021/ol9026705.
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.
描述了桑菊二烯加合物查尔酮（1）和 Mulberrofuran J（2）的每个七甲醚的合成。每个方法中的关键步骤都涉及一种仿生的分子间[4+2] -环加成反应，其中二烯来自于一种异戊烯取代的酚类化合物，而亲二烯体则是查尔酮的α，β-不饱和烯烃。Diels-Alder 反应成功的关键是 2'-羟基查尔酮中游离酚的存在。
