Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 7, Pages 3031-3041Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406020
Keywords
acylation; configuration determination; natural products; peptides; total synthesis
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Funding
- New Energy and Industrial Technology Development Organization (NEDO) of Japan
- Japan Society for the Promotion of Science [25750381]
- Japanese Ministry of Education, Culture, Sports, Science and Technology
- Grants-in-Aid for Scientific Research [25750381] Funding Source: KAKEN
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The total synthesis and stereochemical structural elucidation of JBIR-39, containing four nonproteinogenic piperazic acid (Piz) residues, is reported. The synthesis includes Sc(OTf)(3)-catalyzed acylation of a Piz(gamma-OTBS) derivative with piperazic acid chloride, providing the desired Piz-Piz(gamma-OTBS) dipeptide in high yield without epimerization. After assembling two additional Piz moieties and (S)-isoleucic acid at the N-terminus, amidation with the (R)-alpha-methylserine ester at the C-terminus, and deprotection afforded the desired (2R,8S)-hexapeptide, which is the assumed structure of JBIR-39. Although the spectral data of the (2R,8S)-hexapeptide was not identical to JBIR-39, further synthesis of three stereoisomers confirmed the stereochemical structure of JBIR-39 to be (2S,6S,8S,11R,16S,21R,26S,27S).
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