Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 4, Issue 2, Pages 277-285Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200800382
Keywords
1,3-dipolar cycloaddition; guanidine; oxidation; natural products; total synthesis
Categories
Funding
- JSPS [20310130]
- MEXT [17035025]
- Tokyo University of Agriculture Technology
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Enantioselective total syntheses of (-)- and (+)-decarbamoyloxysaxitoxin (doSTX) and (+)-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 alpha-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.
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