Total synthesis of chiriquitoxin, an analogue of tetrodotoxin isolated from the skin of a dart frog.
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.
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601 (Japan), Fax: (+81) 52-789-4111.
Masaatsu
M
Adachi
Takuya
T
Imazu
Ryo
R
Sakakibara
Yoshiki
Y
Satake
Minoru
M
Isobe
Toshio
T
Nishikawa
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification; D002025:Bufonidae / Q000378:metabolism; D007783:Lactones / Q000737:chemistry; D012867:Skin / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D013779:Tetrodotoxin / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D001688:Biological Products; D007783:Lactones; D013779:Tetrodotoxin; C015741:chiriquitoxin; C116609:3-hydroxybutanal
Pummerer rearrangement; chiriquitoxin; natural products; tetrodotoxin; total synthesis