Convergent and Scalable Synthesis of the ABCDE-Ring Fragment of Caribbean Ciguatoxin C-CTX-1
Makoto Sasaki, Miku Seida, Atsushi Umehara
Abstract
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.
Topics & Concepts
CiguatoxinCiguateraRing (chemistry)Fragment (logic)StereochemistryConvergent synthesisChemistryCoupling (piping)BiologyComputer scienceProgramming languageFisheryMaterials scienceOrganic chemistryFish <Actinopterygii>MetallurgyMarine Toxins and Detection MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions