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- Title
Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog.
- Authors
Adachi, Masaatsu; Imazu, Takuya; Sakakibara, Ryo; Satake, Yoshiki; Isobe, Minoru; Nishikawa, Toshio
- Abstract
The first total synthesis of chiriquitoxin, the most structurally complex analogue of tetrodotoxin isolated from a Costa Rican dart frog, has been accomplished from a newly designed intermediate for a variety of tetrodotoxin derivatives. The synthesis includes the third total synthesis of tetrodotoxin in this laboratory, and its intermediate was transformed into chiriquitoxin by a stereocontrolled aldol reaction with a d-camphor-derived lactone for installation of the unique side chain, and a new deprotection of methylthiomethyl (MTM) ether by using a Pummerer rearrangement.
- Subjects
TETRODOTOXIN; ALDOLS; LACTONES; PUMMERER rearrangement; DENDROBATIDAE
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 5, p1247
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201304110