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.
Amgen, Inc. 1120 Veterans Blvd., South San Francisco, CA 94080, USA.
Paul M
PM
Wehn
J
J
Du Bois
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