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- Title
Total Synthesis, Absolute Configuration, and Phytotoxic Activity of Foeniculoxin.
- Authors
Yamagishi, Akane; Egoshi, Yuki; Fujiwara, Makoto T.; Suzuki, Noriyuki; Taniguchi, Tohru; Itoh, Ryuuichi D.; Suzuki, Yumiko; Masuyama, Yoshiro; Monde, Kenji; Usuki, Toyonobu
- Abstract
Foeniculoxin is a major phytotoxin produced by Italian strains of Phomopsis foeniculi. The first total synthesis is described utilizing the ene reaction and Sonogashira cross‐coupling reaction as key steps. The absolute configuration of the C6' was determined using chiral separation and an advanced Mosher's method. The phytotoxicity of the synthesized compound was demonstrated via syringe‐based infiltration into Chenopodium album and Arabidopsis thaliana leaves. Synthetic foeniculoxin induced various defects in A. thaliana leaf cells before lesion formation, including protein leakage into the cytoplasm from both chloroplasts and mitochondria and mitochondrial rounding and swelling. Furthermore, foeniculoxin and the antibiotic hygromycin B caused similar agglomeration of mitochondria around chloroplasts, highlighting this event as a common component in the early stages of plant cell death.
- Subjects
SONOGASHIRA reaction; ENE reactions; CHEMICAL synthesis; CHENOPODIUM album; ARABIDOPSIS thaliana; PLANT mitochondria
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 8, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202203396