Synthesis of tubuphenylalanines via Ireland-Claisen rearrangement.

TitleSynthesis of tubuphenylalanines via Ireland-Claisen rearrangement.
Publication TypeJournal Article
Year of Publication2013
AuthorsBecker D, Kazmaier U
JournalThe Journal of organic chemistry
Volume78
Issue1
Pagination59-65
Date Published2013 Jan 4
Abstract

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.

DOI10.1016/j.jviromet.2013.02.009
Alternate JournalJ. Org. Chem.