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Synthesis of tubuphenylalanines via Ireland-Claisen rearrangement.
|Title||Synthesis of tubuphenylalanines via Ireland-Claisen rearrangement.|
|Publication Type||Journal Article|
|Year of Publication||2013|
|Authors||Becker D, Kazmaier U|
|Journal||The Journal of organic chemistry|
|Date Published||2013 Jan 4|
The Ireland-Claisen rearrangement is the central step in the synthesis of tubuphenylalanine, a key building block of the highly antitumor-active tubulysins. The rearrangement of substituted β-amino acid allyl esters, in combination with subsequent decarboxylation and oxidative cleavage of the double bond, allows the highly stereoselective introduction of substituents into the α-position of the resulting γ-amino acids.
|Alternate Journal||J. Org. Chem.|