Ontology highlight
ABSTRACT:
SUBMITTER: Nicolaou KC
PROVIDER: S-EPMC4244842 | biostudies-other | 2014 Nov
REPOSITORIES: biostudies-other
Journal of the American Chemical Society 20141106 46
The synthesis of QRSTUVWXYZA' domains 7, 8, and 9 of the highly potent marine neurotoxin maitotoxin (1), the largest secondary metabolite isolated to date, is described. The devised synthetic strategy entailed a cascade Takai-Utimoto ester olefination/ring closing metathesis to construct ring Y, a hydroxydithioketal cyclization/methylation sequence to cast ring X, a Horner-Wadsworth-Emmons coupling of WXYZA' ketophosphonate 11 with QRSTU aldehyde 12 to form enone 10, and a reductive hydroxyketon ...[more]