Asymmetric total synthesis of neoxaline

Tetsuya Ideguchi, Takeshi Yamada, Tatsuya Shirahata, Tomoyasu Hirose, Akihiro Sugawara, Yoshinori Kobayashi, Satoshi Omura, Toshiaki Sunazuka

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.

Original languageEnglish
Pages (from-to)12568-12571
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number34
DOIs
Publication statusPublished - 2013 Aug 28
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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