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JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
Total Synthesis of the Highly N-Methylated Acetylene-Containing Anticancer Peptide Jahanyne.
Organic Letters 2018 Februrary 3
The first total synthesis of the highly N-methylated acetylene-containing lipopeptide jahanyne, an apoptosis-inducing natural product from marine cyanobacteria, is reported. A late-stage solution-phase coupling enabled introduction of the C-terminal ketone pyrrolidine moiety. A modified Fmoc solid-phase synthesis strategy was adopted to effectively couple multiple sterically hindered N-methylated amino acids while suppressing epimerization. The total synthesis has enabled confirmation of the proposed absolute configuration of natural jahanyne.
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