Phosphonoxins II: Diastereoselective synthesis of phosphonic acid analogues of polyoxins

Ding Zhou, Michael Staake, Steven E. Patterson

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

(Chemical Equation Presented) 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)-β- aminophosphonate 3a or (SS,2R,3S,4S)-β-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.

Original languageEnglish (US)
Pages (from-to)2179-2182
Number of pages4
JournalOrganic Letters
Volume10
Issue number11
DOIs
StatePublished - Jun 5 2008

Fingerprint Dive into the research topics of 'Phosphonoxins II: Diastereoselective synthesis of phosphonic acid analogues of polyoxins'. Together they form a unique fingerprint.

Cite this