Synthesis of the octahydroindole unit of aeruginosins via asymmetric hydrogenation of the Diels-Alder adducts of 2-amido-2,4-pentadienoate

Yoichiro Hoshina, Takayuki Doi, Takashi Takahashi

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

An optically active octahydroindole, the core unit of aeruginosins (Choi) was synthesized. The Diels-Alder reaction of Danishefsky's diene with methyl (Z)-2-acetamido-2,4-pentadienoates provided the adducts regioselectively in good yield. The adducts were converted to the l-Choi precursor by asymmetric hydrogenation, followed by acid cyclization.

Original languageEnglish
Pages (from-to)12740-12746
Number of pages7
JournalTetrahedron
Volume63
Issue number51
DOIs
Publication statusPublished - 2007 Dec 17
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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