Diazonamide support studies: stereoselective formation of the C10 chiral center in both the CDEFG and AEFG fragments.
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.
Lin
Jinzhen
J
Department of Chemistry and Biochemistry, University of California at Santa Cruz, Santa Cruz, California 95064, USA.
Gerstenberger
Brian S
BS
Stessman
Nhu Y T
NY
Konopelski
Joseph P
JP
D001572:Benzofurans / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry*; D000078183:Oxindoles; D013237:Stereoisomerism; D013379:Substrate Specificity; D014443:Tyrosine / Q000737:chemistry
D001572:Benzofurans; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D010080:Oxazoles; D000078183:Oxindoles; C022960:2-oxindole; C408862:diazonamide A; D014443:Tyrosine; C105430:benzofuran