Phosphonoxins II: diastereoselective synthesis of phosphonic acid analogues of polyoxins.
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.
Zhou
Ding
D
Center for Drug Design, Academic Health Center, university of Minnesota, Minneapolis, Minnesota 55455, USA.
Staake
Michael
M
Patterson
Steven E
SE
D063065:Organophosphonates / Q000737:chemistry*; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D063065:Organophosphonates; D011741:Pyrimidine Nucleosides; C530330:phosphonoxin B1; C530331:phosphonoxin B2; C002457:polyoxin