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Total synthesis of riccardin C and (±)-cavicularin via Pd-catalyzed Ar–Ar cross couplings
Tetrahedron ( IF 2.1 ) Pub Date : 2013-06-24 , DOI: 10.1016/j.tet.2013.06.064
Kenichi Harada , Kosho Makino , Naoki Shima , Haruka Okuyama , Tomoyuki Esumi , Miwa Kubo , Hideaki Hioki , Yoshinori Asakawa , Yoshiyasu Fukuyama

Riccardin C, a specific LXRα agonist, is a representative macrocyclic bisbibenzyl-type natural product. As part of our synthetic studies on macrocyclic bisbibenzyls, the synthesis of riccardin C and its analog cavicularin was examined. The total synthesis of riccardin C was accomplished via a Pd-catalyzed intramolecular Suzuki–Miyaura coupling as the key macrocyclization step. This synthetic strategy was also extended in the synthesis of (±)-cavicularin, which was then attained by constructing the dihydrophenanthrene moiety using a Pd-catalyzed Ar–Ar coupling reaction.



中文翻译:

Pd催化的Ar–Ar交叉偶联全合成蓖麻毒素C和(±)-cavicularin

Riccardin C是一种特定的LXRα激动剂,是一种代表性的大环双联二苄基型天然产物。作为我们对大环双联苄的合成研究的一部分,研究了蓖麻毒素C及其类似物卡维霉素的合成。riccardin C的总合成是通过Pd催化的分子内Suzuki-Miyaura偶联作为关键的大环化步骤而完成的。这种合成策略也扩展到(±)-cavicularin的合成中,然后通过使用Pd催化的Ar-Ar偶联反应构建二氢菲部分来实现。

更新日期:2013-06-24
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