Total synthesis of (+)-decarbamoylsaxitoxin and (+)-gonyautoxin 3.
Facile construction of the complex saxitoxin (STX) skeleton is carried out by using a novel, conformationally controlled, guanidine cyclization process that relies on the use of neighboring group participation. The utility of this methodology is verified by its employment in syntheses of both natural and unnatural STX derivatives.
Iwamoto
Osamu
O
Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo 184-8588, Japan.
Nagasawa
Kazuo
K
D003500:Cyclization; D008958:Models, Molecular; D012530:Saxitoxin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D012530:Saxitoxin; C076432:decarbamoylneosaxitoxin; C013007:gonyautoxins