Song Zhenlei, Hsung Richard P, Lu Ting, Lohse Andrew G
Division of Pharmaceutical Sciences and Department of Chemistry, Rennebohm Hall, 777 Highland Avenue, University of Wisconsin, Madison, Wisconsin 53705, USA.
J Org Chem. 2007 Dec 7;72(25):9722-31. doi: 10.1021/jo7017922. Epub 2007 Nov 3.
A detailed account on the stereoselective synthesis of the C1-C9 subunit of (+)-zincophorin is described here. This approach features the first application of a stereoselective inverse electron demand hetero-[4 + 2] cycloaddition of chiral allenamides in natural product synthesis. The C1-C9 subunit matches Cossy's intermediate, thereby constituting a formal total synthesis. In addition, details of an unusual urea-directed Stork-Crabtree hydrogenation observed during these efforts are also disclosed here.
本文详细描述了(+)-锌霉素C1-C9亚基的立体选择性合成。该方法的特点是在手性丙二烯酰胺的立体选择性逆电子需求杂环[4+2]环加成反应首次应用于天然产物合成中。C1-C9亚基与Cossy的中间体匹配,从而构成了形式上的全合成。此外,本文还披露了在这些研究过程中观察到的一种不寻常的脲导向的Stork-Crabtree氢化反应的细节。