Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 25, Pages 7586-7595Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000497
Keywords
cyclization; gambierol; oxiranyl anions; polycyclic ethers; ring expansion
Categories
Funding
- Ministry of Education, Culture, Sports, Science, and Technology [18032079, 21590029]
Ask authors/readers for more resources
Gambierol was isolated as a neurotoxin from the cultured cells of the ciguatera causative dinoflagellate Gambierdiscus toxicus and classified as a member of the polycyclic ether family of marine toxins. The structure consists of a ladder-shaped trans-fused octacyclic ring system that includes 18 stereogenic centers, two 1,3-diaxial dimethyl-substituted tetrahydropyranyl rings, and a partially conjugated triene side chain. The total synthesis of gambierol has been achieved by utilizing an oxiranyl anion strategy in an iterative manner. Synthetic highlights of this route include direct carbon carbon formation on epoxides, sulfonyl-assisted 6-endo cyclization, and an expansion reaction of the tetrahydropyranyl rings to oxepanes to forge the polycyclic architecture of the target molecule.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available