1. Total Synthesis of Miuraenamides A and D
- Author
-
Koh Tohyama, Daisuke Ojima, Arihiro Iwasaki, Makoto Ojika, Kayoko Ito, Ayano Yasui, Keita Tokuzumi, Eisuke Toriihara, Kiyotake Suenaga, and Tomohiko Tomura
- Subjects
Depsipeptide ,Phytophthora ,Spectrometry, Mass, Electrospray Ionization ,010405 organic chemistry ,Stereochemistry ,Longest linear sequence ,Electrospray ionization ,Proton Magnetic Resonance Spectroscopy ,Organic Chemistry ,Epoxide ,Total synthesis ,010402 general chemistry ,Antimicrobial ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Yield (chemistry) ,Depsipeptides ,Moiety ,Humans ,Carbon-13 Magnetic Resonance Spectroscopy ,Cell Proliferation ,HeLa Cells - 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.
- Published
- 2016