A stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A.
Weaving an intricate web: A stereoselective synthesis of (-)-agelastatin A has been developed, which requires 11 steps from commercially available starting material. The application of a Rh-catalyzed intramolecular olefin aziridination reaction and the subsequent manipulation of the resulting tricyclic intermediate (see scheme) punctuate this study.
Wehn
Paul M
PM
Amgen, Inc. 1120 Veterans Blvd., South San Francisco, CA 94080, USA.
Du Bois
J
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D017605:Bromine Compounds / Q000737:chemistry*; D002384:Catalysis; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry*; D012235:Rhodamines / Q000737:chemistry; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000737:chemistry; D013841:Thiazepines / Q000737:chemistry
D000470:Alkaloids; D001688:Biological Products; D017605:Bromine Compounds; D006573:Heterocyclic Compounds, 1-Ring; D023303:Oxazolidinones; D011758:Pyrroles; D012235:Rhodamines; D013451:Sulfonic Acids; D013841:Thiazepines; C464968:agelastatin A; C517814:oxathiane; C005741:sulfamic acid