Synthetic study of azaspiracid-1: Synthesis of the EFGHI-ring fragment

Masato Oikawa, Tomoko Uehara, Taizo Iwayama, Makoto Sasaki

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Here, we report a synthesis of the lower half C21-C40 fragment of the shellfish toxin, azaspiracid-1. The C28-C 40 fragment was synthesized by a coupling between the C 28-C35 epoxide and the C36-C40 dithioacetal anion, followed by the HI-ring spiroaminal formation. An aldehyde corresponding to the C28-C40 fragment was then coupled with the C21-C27 allylic stannane by using InCl 3. Finally, the FG-ring was constructed by HF-pyridine to accomplish the synthesis of the suitably protected C21-C40 fragment.

Original languageEnglish
Pages (from-to)3943-3946
Number of pages4
JournalOrganic letters
Volume8
Issue number18
DOIs
Publication statusPublished - 2006 Aug 31

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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