title: Phosphonoxins II: diastereoselective synthesis of phosphonic acid analogues of polyoxins.
abstract: A diastereoselective synthesis of polyoxin analogues termed phosphonoxin B1 and B2 has been achieved. The key step was sulfinimine-mediated asymmetric formation of ( RS ,2S,3S,4S)-beta-aminophosphonate 3a or (SS ,2R,3S,4S)-beta-aminophosphonate 7 as the major diastereoisomer. A double stereodifferentiation effect was not observed, and the diastereoselectivity is controlled by the absolute configuration of the sulfinyl group.
authors.affiliation: Center for Drug Design, Academic Health Center, university of Minnesota, Minneapolis, Minnesota 55455, USA.
authors.forename: Ding
authors.initials: D
authors.lastname: Zhou
authors.forename: Michael
authors.initials: M
authors.lastname: Staake
authors.forename: Steven E
authors.initials: SE
authors.lastname: Patterson
mesh_terms: D063065:Organophosphonates / Q000737:chemistry*; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D063065:Organophosphonates; D011741:Pyrimidine Nucleosides; C530330:phosphonoxin B1; C530331:phosphonoxin B2; C002457:polyoxin