Phosphonoxins II: Diastereoselective synthesis of phosphonic acid analogues of polyoxins

Ding Zhou; Michael Staake; Steven E. Patterson

doi:10.1021/ol800552k

Phosphonoxins II: Diastereoselective synthesis of phosphonic acid analogues of polyoxins

Ding Zhou, Michael Staake, Steven E. Patterson

Center for Drug Design

Research output: Contribution to journal › Article › peer-review

10 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 (S_S,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 language	English (US)
Pages (from-to)	2179-2182
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	11
DOIs	https://doi.org/10.1021/ol800552k
State	Published - Jun 5 2008

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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.",

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AU - Zhou, Ding

AU - Staake, Michael

AU - Patterson, Steven E.

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N2 - (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.

AB - (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.

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Phosphonoxins II: Diastereoselective synthesis of phosphonic acid analogues of polyoxins

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