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

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Depsipeptides
Epoxy Compounds
Cell growth
Acids
miuraenamide A

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Ojima, D., Yasui, A., Tohyama, K., Tokuzumi, K., Toriihara, E., Ito, K., ... 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

Total Synthesis of Miuraenamides A and D. / Ojima, Daisuke; Yasui, Ayano; Tohyama, Koh; Tokuzumi, Keita; Toriihara, Eisuke; Ito, Kayoko; Iwasaki, Arihiro; Tomura, Tomohiko; Ojika, Makoto; Suenaga, Kiyotake.

In: Journal of Organic Chemistry, Vol. 81, No. 20, 21.10.2016, p. 9886-9894.

Research output: Contribution to journalArticle

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, vol. 81, no. 20, pp. 9886-9894. https://doi.org/10.1021/acs.joc.6b02061
Ojima D, Yasui A, Tohyama K, Tokuzumi K, Toriihara E, Ito K et al. Total Synthesis of Miuraenamides A and D. Journal of Organic Chemistry. 2016 Oct 21;81(20):9886-9894. https://doi.org/10.1021/acs.joc.6b02061
Ojima, Daisuke ; Yasui, Ayano ; Tohyama, Koh ; Tokuzumi, Keita ; Toriihara, Eisuke ; Ito, Kayoko ; Iwasaki, Arihiro ; Tomura, Tomohiko ; Ojika, Makoto ; Suenaga, Kiyotake. / Total Synthesis of Miuraenamides A and D. In: Journal of Organic Chemistry. 2016 ; Vol. 81, No. 20. pp. 9886-9894.
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