Carmichael Rachael A, Chalifoux Wesley A
Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, NV, 89557, USA.
Chemistry. 2016 Jun 20;22(26):8781-5. doi: 10.1002/chem.201601850. Epub 2016 May 17.
The construction of complex polycyclic terpenoid products in an efficient and step-economical manner using multicomponent and tandem processes is highly valuable. Herein, we report a tandem cyclization sequence that initiates with a multicomponent double Diels-Alder reaction of cross-conjugated diynones, followed by a Nazarov cyclization to efficiently produce [6-5-6] tricyclic products with excellent regio- and diastereoselectivity. This methodology generates five new carbon-carbon bonds, three rings, quaternary or vicinal quaternary carbons, and stereogenic centers in a one-pot reaction.
利用多组分和串联反应以高效且步骤经济的方式构建复杂的多环萜类产物具有很高的价值。在此，我们报道了一种串联环化序列，该序列起始于交叉共轭二炔酮的多组分双狄尔斯-阿尔德反应，随后进行纳扎罗夫环化，以优异的区域和非对映选择性高效地生成[6-5-6]三环产物。该方法在一锅反应中生成五个新的碳-碳键、三个环、季碳或邻位季碳以及立体中心。
