Total synthesis of (-)-rhazinilam using 1,3-dipolar cycloaddition of optically active münchnone intermediate

Kenji Sugimoto, Yuta Miyakawa, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

A concise stereocontrolled total synthesis of (-)-rhazinilam was achieved by the regioselective 1,3-dipolar cycloaddition of a fully elaborated optically active münchnone intermediate prepared from d-aspartic acid dimethyl ester. The regiochemistry of the 1,3-dipolar cycloaddition of münchnone intermediate to various arylacetylenes was also investigated.

Original languageEnglish
Pages (from-to)3619-3624
Number of pages6
JournalTetrahedron
Volume71
Issue number22
DOIs
Publication statusPublished - 2015 Jun 3

Keywords

  • 1,3-Dipolar cycloaddition
  • Alkaloids
  • Münchnone
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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