Studies toward diazonamide A: initial synthetic forays directed toward the originally proposed structure.
A brief introduction into the chemistry of diazonamide A (1) is followed by first-generation sequences to access the originally proposed structure for this unusual marine natural product. These explorations identified a route capable of delivering a model compound possessing the complete heteroaromatic core of the natural product, highlighting in the process several unanticipated synthetic challenges which led both to new methodology as well as an improved synthetic plan that was successfully applied to fully functionalized intermediates.
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. kcn@scripps.edu
Snyder
Scott A
SA
Huang
Xianhai
X
Simonsen
Klaus B
KB
Koumbis
Alexandros E
AE
Bigot
Antony
A
D004815:Epidermal Growth Factor / 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*; D010446:Peptide Fragments / Q000737:chemistry
D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D010080:Oxazoles; D010446:Peptide Fragments; C408862:diazonamide A; D004815:Epidermal Growth Factor