Synthesis of Saxitoxin and Its Derivatives

Yuya Okuyama, Ryosuke Okamoto, Shori Mukai, Kyoko Kinoshita, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)


The chiral synthesis of (+)-saxitoxin and its derivatives is described. Two consecutive carbon−nitrogen bonds at C-5 and C-6 in saxitoxin were effectively installed by the sequential Overman rearrangement of an allylic vicinal diol derived from D-malic acid. The bicyclic guanidine unit was constructed by the intramolecular aminal formation of an acyclic bis-guanidine derivative possessing a ketone carbonyl at C-4. From the bicyclic aminal intermediate, (+)-saxitoxin, (+)-decarbamoyl-β-saxitoxinol [(+)-dc-β-saxitoxinol], and the unnatural skeletal isomer, (−)-isodc-saxitoxinol, were synthesized.

Original languageEnglish
Pages (from-to)8697-8701
Number of pages5
JournalOrganic Letters
Issue number21
Publication statusPublished - 2020 Nov 6

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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