Unified synthesis of the DEF and GhI ring systems of maitotoxin

Takaya Yasudomi, Hiroyuki Yakushiji, Kohei Torikai, Makoto Ebine, Tohru Oishi

Research output: Contribution to journalArticle

Abstract

Unified synthesis of 6/6/6-tricyclic ethers corresponding to the DEF and GHI ring systems of maitotoxin was achieved from a common intermediate prepared from a furan derivative and a terminal olefin via FujiwaraMoritani reaction, followed by Sharpless asymmetric dihydroxylation, and Achmatowicz reaction. The DEF ring was synthesized from the common intermediate via regio- and stereoselective borylation of an enone, and methylation of an S, O-acetal. On the other hand, the GHI ring was synthesized from the common intermediate via reductive etherification, Sharpless asymmetric dihydroxylation, and BartonMcCombie deoxygenation.

Original languageEnglish
Pages (from-to)1156-1159
Number of pages4
JournalChemistry Letters
Volume48
Issue number9
DOIs
Publication statusPublished - Jan 1 2019

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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