Formal Synthesis of Lobatamides A and C
Lobatamides, featuring a unique 15-membered dilactone core, are a family of marine natural products isolated from the tunicate <i>Aplidium lobatum</i> and exhibit inhibitory activity against mammalian vacuolar-type proton pump ATPase (V-ATPase). Herein, we report an alternative route to Sato's intermediate, achieving formal syntheses of lobatamides A and C. Key steps include the palladium-catalyzed Suzuki-Miyaura coupling reaction to give a salicylic acid derivative containing a trisubstituted (<i>Z</i>)-olefin and the Nozaki-Hiyama-Takai-Kishi (NHTK) reaction to construct the 15-membered dilactone core.
Authors
- Masaki Kanakogi
- Takumi Fukuda (ORCID: https://orcid.org/0000-0003-3735-8017)
- Ryo Fujii
- Yuki NAKAHARA
- Ryo Takita (ORCID: https://orcid.org/0000-0003-4104-9890)
- Yoshitaka Hamashima (ORCID: https://orcid.org/0000-0002-6509-8956)
- Hitoshi Ouchi (ORCID: https://orcid.org/0000-0001-6519-0990)
- Toshiyuki Kan (ORCID: https://orcid.org/0000-0002-9709-6365)
- Fumihiko Yoshimura (ORCID: https://orcid.org/0000-0002-1187-6062)
- Makoto Inai (ORCID: https://orcid.org/0000-0001-7074-0520)
Institutions
- University of Shizuoka (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-17
- DOI
- https://doi.org/10.1021/acs.orglett.5c00739
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Japan Agency for Medical Research and Development
- Pharmaceutical Society of Japan
- Shizuoka University
- Japan Society for the Promotion of Science