Total synthesis of (-)-5,6,11-trideoxytetrodotoxin and its 4-epimer

Taiki Umezawa; Toshihiro Hayashi; Hiroshi Sakai; Hidetoshi Teramoto; Takeshi Yoshikawa; Masashi Izumida; Yoshinori Tamatani; Tadashi Hirose; Yasufumi Ohfune; Tetsuro Shinada

doi:10.1021/ol062098d

Total synthesis of (-)-5,6,11-trideoxytetrodotoxin and its 4-epimer

Org Lett. 2006 Oct 12;8(21):4971-4. doi: 10.1021/ol062098d.

Authors

Taiki Umezawa¹, Toshihiro Hayashi, Hiroshi Sakai, Hidetoshi Teramoto, Takeshi Yoshikawa, Masashi Izumida, Yoshinori Tamatani, Tadashi Hirose, Yasufumi Ohfune, Tetsuro Shinada

Affiliation

¹ Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan.

PMID: 17020349
DOI: 10.1021/ol062098d

Abstract

[reaction: see text] The first total synthesis of 5,6,11-trideoxytetrodotoxin (1) and its 4-epimer were achieved. The synthesis is characterized by the stereoselective construction of the quaternary amino carbon center at C8a by an asymmetric transferring Strecker synthesis and the highly efficient conversion of cyanohydrin 4 to 1 via intramolecular cyclization reactions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Molecular Structure
Nitriles / chemistry*
Stereoisomerism
Tetrodotoxin / analogs & derivatives*
Tetrodotoxin / chemical synthesis
Tetrodotoxin / chemistry

Substances

5,6,11-trideoxytetrodotoxin
Nitriles
cyanohydrin
Tetrodotoxin