1003193-13-2Relevant academic research and scientific papers
Total synthesis of (-)- and (+)-decarbamoyloxysaxitoxin and (+-)-saxitoxin
Iwamoto, Osamu,Shinohara, Ryoko,Nagasawa, Kazuo
scheme or table, 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.
Total synthesis of (-)-decarbamoyloxysaxitoxin
Iwamoto, Osamu,Koshino, Hiroyuki,Hashizume, Daisuke,Nagasawa, Kazuo
, p. 8625 - 8628 (2008/09/18)
(Chemical Equation Presented) A facile and general synthetic strategy for saxitoxin derivatives has been developed, as exemplified by the efficient synthesis of (-)-decarbamoyloxysaxitoxin ((-)-doSTX), the putative enantiomer of the natural product, in 17
