Title
Synthesis of the Aminovinylcysteine-Containing C-Terminal Macrocycle of the Linaridins
Document Type
Article
Publication Date
3-6-2020
Abstract
-Phthalimido-d-cysteine allyl ester was -alkylated with 2-iodoethanol. The derived β-thioaldehyde was condensed with α-tetrachlorophthalimidovalinamide to afford a -thioenamide. Removal of the tetrachlorophthalimido protecting group and homologation with -Boc-l-leucine afforded the linear tripeptide. Removal of the Boc and allyl protecting groups, followed by carbodiimide-mediated cyclization, led to the 13-membered ring with the aminovinylcysteine moiety embedded. This constitutes the C-terminal macrocycle of all known members of the linardin family of peptides, including the antileukemia agent, cypemycin.
Publication Source (Journal or Book title)
Organic letters
First Page
1874
Last Page
1877
Recommended Citation
Lutz, J. A., & Taylor, C. M. (2020). Synthesis of the Aminovinylcysteine-Containing C-Terminal Macrocycle of the Linaridins. Organic letters, 22 (5), 1874-1877. https://doi.org/10.1021/acs.orglett.0c00218