Convergent and Scalable Synthesis of the ABCDE-Ring Fragment of Caribbean Ciguatoxin C‑CTX‑1

• Main Authors: Makoto Sasaki (71218), Miku Seida (14283732), Atsushi Umehara (1814875)
• Format: Other Non-Article Part of Journal/Newspaper
• Language: unknown
• Published: 2022
• Subjects: Biochemistry; Microbiology; Cell Biology; Neuroscience; Physiology; Pharmacology; Ecology; Sociology; Marine Biology; Infectious Diseases; Chemical Sciences not elsewhere classified; tempo )/ phi; oac )< sub; northeast atlantic areas; major causative toxin; caribbean ciguatoxin c; ring skeleton via; tetramethyl piperidine 1; convergent fragment coupling; ring fragment; caribbean sea; ring system; synthesis include; scalable synthesis; key features; iterative use; ciguatera poisoning; Northeast Atlantic
• Online Access: https://doi.org/10.1021/acs.joc.2c02414.s001

Convergent and scalable synthesis of the ABCDE-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera poisoning in the Caribbean Sea and the Northeast Atlantic areas, is described in detail. The key features of the synthesis include an iterative use of 2,2,6,6-tetramethyl piperidine 1-oxyl (TEMPO)/PhI(OAc) 2 -mediated oxidative lactonization and Suzuki–Miyaura coupling en route to the DE-ring system and a convergent fragment coupling to form the ABCDE-ring skeleton via the Suzuki–Miyaura coupling strategy.