Total Synthesis of Miuraenamides A and D

Daisuke Ojima, Ayano Yasui, Koh Tohyama, Keita Tokuzumi, Eisuke Toriihara, Kayoko Ito, Arihiro Iwasaki, Tomohiko Tomura, Makoto Ojika, Kiyotake Suenaga

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Miuraenamides A and D, cyclodepsipeptides with antimicrobial and antitumor activity, were synthesized. The synthesis of an unsaturated hydroxycarboxylic acid moiety, starting from a chiral epoxide, was achieved by Suzuki-Miyaura coupling as a key step. As a result, the overall yield for miuraenamide A over the longest linear sequence is 3.2%, while the yield of the previously reported procedure is 1.9%. In addition, the cell growth-inhibitory activity and anti-Phytophthora activity of the synthesized compounds were evaluated.

Original languageEnglish
Pages (from-to)9886-9894
Number of pages9
JournalJournal of Organic Chemistry
Volume81
Issue number20
DOIs
Publication statusPublished - 2016 Oct 21

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Total Synthesis of Miuraenamides A and D'. Together they form a unique fingerprint.

  • Cite this

    Ojima, D., Yasui, A., Tohyama, K., Tokuzumi, K., Toriihara, E., Ito, K., Iwasaki, A., Tomura, T., Ojika, M., & Suenaga, K. (2016). Total Synthesis of Miuraenamides A and D. Journal of Organic Chemistry, 81(20), 9886-9894. https://doi.org/10.1021/acs.joc.6b02061