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Diazonamide Support Studies: Stereoselective Formation of the C10 Chiral Center in both the CDEFG and AEFG Fragments

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journal contribution
posted on 18.09.2008, 00:00 by Jinzhen Lin, Brian S. Gerstenberger, Nhu Y T. Stessman, Joseph P. Konopelski
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.