title: Diastereocontrolled construction of pactamycin's complex ureido triol functional array.
abstract: An advanced intermediate in a projected synthesis of pactamycin has been prepared. Early installation of the C1-dimethylurea functionality allows for its participation in a diastereoselective, chelation-controlled addition of organometal nucleophiles to the C5 prochiral ketone. Four of the molecule's six stereocenters are set with a ketone functional handle provided for subsequent manipulation.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: Justin T
authors.initials: JT
authors.lastname: Malinowski
authors.forename: Stefan J
authors.initials: SJ
authors.lastname: McCarver
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D008782:Methylurea Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010142:Pactamycin / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000903:Antibiotics, Antineoplastic; D007659:Ketones; D008782:Methylurea Compounds; D010142:Pactamycin; C018275:1,1-dimethylurea