In the preceding paper' we have reported a practical preparation of the Diels-Alder adduct II from S-(a-oximinoethyl)toluquinone and butadiene. We would like to colmnunicate a derivation of II into XIX, which has the same six chiral centers on the cyclohexane ring as tetrodotoxin (I) has.
Synthetic studies on tetrodotoxin (1) stereocontrolled synthesis of the cyclohexane moiety
โ Scribed by Minoru Isobe; Toshio Nishikawa; Stanislaw Pikul; Toshio Goto
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 286 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
โฆ Synopsis
Tetrodotoxin is a potent neurotoxin, for which we planned a chemical
๐ SIMILAR VOLUMES
A stereocontrolled and practical synthetic route to the acetal 2a, a degradation product of palytoxin, in optically active form is described. Palytoxin, the toxic principle isolated from marine soft corals of the genus Palythoa, is the most poisonous substance known to date, except for a few polype
An 8-step synthesis of the bicyclic ketal 2 from l-(+)-citronella1 is described. -
A stereocontrolled 12-step synthesis of the C.85-C.98 segment of palytoxin is described, Recent work in this laboratory has established the complete structure and laid a solid foundation for the chemical synthesis of the structurally novel and highly physioloqically active marine natural product pal
An asymmetric synthesis of the tricyclic dihyctrofuran moiety of azadirachtin is reported. The Diels-Alder adduct, which was catalyzed by Evans' chiral Cu-bisoxazoline complex, was easily converted to the tricyclic portion via SmI 2 reductive cleavage and selective functionalization.