Total Synthesis and Determination of the Absolute Configuration of Shodoamide C: An Amphotericin B Potentiator against <i>Candida albicans</i>
The total synthesis and structural determination of shodoamide C (<b>1</b>), a compound that enhances the activity of amphotericin B against <i>Candida albicans</i>, have been achieved. A synthetic strategy for compound <b>1</b> facilitated the efficient synthesis of all 16 stereoisomers, allowing for the identification of the four previously unknown stereocenters of <b>1</b> through the chiral recycle HPLC analyses. All stereoisomers of <b>1</b> showed similar activity, indicating that their stereochemistries minimally influenced it.
Authors
- Hiroshi Tomoda (ORCID: https://orcid.org/0000-0002-1241-8901)
- Akihiro Hirata
- Shinya Ueki
- Tohru Nagamitsu (ORCID: https://orcid.org/0000-0002-4278-4507)
- Akiho Yagi (ORCID: https://orcid.org/0009-0008-4845-6791)
- Ryuji Uchida (ORCID: https://orcid.org/0000-0002-1864-8273)
- Masaki Ohtawa (ORCID: https://orcid.org/0000-0001-7129-012X)
- Masahiro Iwahori
Institutions
- Kitasato University (JP)
- Tohoku Medical and Pharmaceutical University (JP)
- Komatsu (Japan) (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-02
- DOI
- https://doi.org/10.1021/acs.orglett.5c01017
- Citations
- 1
- Primary Topic
- Antifungal resistance and susceptibility
- Type
- article
- Field-Weighted Citation Impact
- 1.40