A convergent total synthesis of ustiloxin D via an unprecedented copper-catalyzed ethynyl aziridine ring-opening by phenol derivatives.
[reaction: see text] The ustiloxins are a family of heterodetic cyclopeptides that have been isolated from the water extracts of false smut balls on the panicles of rice plants caused by the fungus Ustilaginoidea virens. A concise total synthesis of ustiloxin D has been achieved via an unprecedented ethynyl aziridine ring-opening of phenol derivatives. The longest linear sequence of the synthesis is 15 steps from commercially available compounds.
Li
Pixu
P
Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, Pennsylvania 19104, USA.
Evans
Cory D
CD
Joullié
Madeleine M
MM
D001388:Aziridines / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009183:Mycotoxins / Q000138:chemical synthesis*; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D010636:Phenols / Q000737:chemistry
D001388:Aziridines; D009183:Mycotoxins; D010456:Peptides, Cyclic; D010636:Phenols; C089079:ustiloxin D; D003300:Copper