Synthesis of Saxitoxin and Its Derivatives

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

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

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, (-)-iso-dc-saxitoxinol, were synthesized.

Original languageEnglish
JournalOrganic Letters
DOIs
Publication statusAccepted/In press - 2020

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis of Saxitoxin and Its Derivatives'. Together they form a unique fingerprint.

Cite this