First asymmetric total synthesis of (−)-isostemonamine and kinetic analysis of its isomerizations

Takayuki Iwata, Taishi Tomiyama, Satoshi Fujita, Mitsuru Shindo

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The first asymmetric total synthesis of (−)-isostemonamine is reported herein. The key reactions include the regioselective oxidation of the diketone, which is reported to be an intermediate in our synthesis of (−)-stemonamine. The chiral high-performance liquid chromatography (HPLC) analysis of the racemization and epimerization of (−)-isostemonamine revealed that isostemonamine isomerizes significantly faster than stemonamine.

Original languageEnglish
Pages (from-to)712-718
Number of pages7
JournalHeterocycles
Volume97
Issue number2
DOIs
Publication statusPublished - Jan 1 2018

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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