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 journalArticlepeer-review

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

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