Convenient synthesis and diversification of dehydroalaninyl phosphinic peptide analogues

Magdalini Matziari; Dimitris Georgiadis; Vincent Dive; Athanasios Yiotakis

doi:10.1021/ol0069103

Convenient synthesis and diversification of dehydroalaninyl phosphinic peptide analogues

Magdalini Matziari, Dimitris Georgiadis, Vincent Dive, Athanasios Yiotakis^*

^*Corresponding author for this work

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

50 Citations (Scopus)

Abstract

Equation presented Dehydroalaninyl phosphinic dipeptide analogues were synthesized, via an efficient tandem Arbuzov addition/allylic rearrangement, in high yields. The susceptibility of the conjugate system to 1,4 nucleophilic additions was investigated. C-Elongation of the dipeptides was performed, and the efficiency of 1,4 addition to the resulting acrylamidic moiety was evaluated. Derivatization of such phosphinic templates is a powerful approach for rapid access to large number of phosphinic pseudopeptides bearing various side chains in the P₁′ position.

Original language	English
Pages (from-to)	659-660
Number of pages	2
Journal	Organic Letters
Volume	3
Issue number	5
DOIs	https://doi.org/10.1021/ol0069103
Publication status	Published - 8 Mar 2001
Externally published	Yes

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abstract = "Equation presented Dehydroalaninyl phosphinic dipeptide analogues were synthesized, via an efficient tandem Arbuzov addition/allylic rearrangement, in high yields. The susceptibility of the conjugate system to 1,4 nucleophilic additions was investigated. C-Elongation of the dipeptides was performed, and the efficiency of 1,4 addition to the resulting acrylamidic moiety was evaluated. Derivatization of such phosphinic templates is a powerful approach for rapid access to large number of phosphinic pseudopeptides bearing various side chains in the P1′ position.",

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AU - Matziari, Magdalini

AU - Georgiadis, Dimitris

AU - Dive, Vincent

AU - Yiotakis, Athanasios

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N2 - Equation presented Dehydroalaninyl phosphinic dipeptide analogues were synthesized, via an efficient tandem Arbuzov addition/allylic rearrangement, in high yields. The susceptibility of the conjugate system to 1,4 nucleophilic additions was investigated. C-Elongation of the dipeptides was performed, and the efficiency of 1,4 addition to the resulting acrylamidic moiety was evaluated. Derivatization of such phosphinic templates is a powerful approach for rapid access to large number of phosphinic pseudopeptides bearing various side chains in the P1′ position.

AB - Equation presented Dehydroalaninyl phosphinic dipeptide analogues were synthesized, via an efficient tandem Arbuzov addition/allylic rearrangement, in high yields. The susceptibility of the conjugate system to 1,4 nucleophilic additions was investigated. C-Elongation of the dipeptides was performed, and the efficiency of 1,4 addition to the resulting acrylamidic moiety was evaluated. Derivatization of such phosphinic templates is a powerful approach for rapid access to large number of phosphinic pseudopeptides bearing various side chains in the P1′ position.

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Convenient synthesis and diversification of dehydroalaninyl phosphinic peptide analogues

Abstract

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