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Diazonamide support studies: stereoselective formation of the C10 chiral center in both the CDEFG and AEFG fragments.

ABSTRACT: 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.

SUBMITTER: Lin J

PROVIDER: S-EPMC2638117 | biostudies-literature | 2008 Sep

REPOSITORIES: biostudies-literature

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Diazonamide support studies: stereoselective formation of the C10 chiral center in both the CDEFG and AEFG fragments.

Lin Jinzhen J Gerstenberger Brian S BS Stessman Nhu Y T NY Konopelski Joseph P JP

Organic letters 20080815 18

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. ...[more]

PMID: 18702502

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