Lin Jinzhen, Gerstenberger Brian S, Stessman Nhu Y T, Konopelski Joseph P
Department of Chemistry and Biochemistry, University of California at Santa Cruz, Santa Cruz, California 95064, USA.
Org Lett. 2008 Sep 18;10(18):3969-72. doi: 10.1021/ol8014336. Epub 2008 Aug 15.
The synthesis of both the AEFG macrolactam and the CDEFG bis-indole/tyrosine units found in the marine natural product diazonamide A is presented. Key to the success of the synthesis is the highly stereoselective direct C-arylation of an oxindole by an aryllead(IV) reagent derived from tyrosine.
介绍了海洋天然产物重氮酰胺A中AEFG大环内酰胺和CDEFG双吲哚/酪氨酸单元的合成。合成成功的关键是酪氨酸衍生的芳基铅(IV)试剂对氧化吲哚进行高度立体选择性的直接C-芳基化反应。