1185281-47-3Relevant academic research and scientific papers
Total synthesis of (+)-decarbamoylsaxitoxin and (+)-gonyautoxin 3
Iwamoto, Osamu,Nagasawa, Kazuo
supporting information; experimental part, p. 2150 - 2153 (2010/08/05)
Figure presented 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.
Total synthesis of (-)- and (+)-decarbamoyloxysaxitoxin and (+-)-saxitoxin
Iwamoto, Osamu,Shinohara, Ryoko,Nagasawa, Kazuo
experimental part, p. 277 - 285 (2010/04/23)
Enantioselective total syntheses of (-)- and (-1-)-decarbamoyloxysaxitoxin (doSTX) and (-l-)-saxitoxin (STX) were achieved. The characteristic spiro-fused cyclic guanidine structure of STX was constructed by oxidation at the C4 position with IBX via an α-iminium carbonyl intermediate and acid-promoted cyclization of guanidine at the C5 position. A second-generation methodology was developed for the synthesis of STX, featuring discriminative reduction of the nitro group and N-O bond in nitroisoxazolidine. This approach provides efficient access to the key diamine intermediate for STXs.
