Formal total synthesis of (-)-physostigmine

Kaori Asakawa, Naoyoshi Noguchi, Masahisa Nakada

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Abstract

The formal total synthesis of (-)-physostigmine via the chiral malonic acid mono-ester ((R)-2-(2-chlorophenyl)-2-methoxycarbonylpropanoic acid, 99% ee) newly prepared by the pig liver esterase (PLE) mediated asymmetric hydrolysis of the corresponding di-ester is described. The CuI-mediated intramolecular aryl amidation under modified Buchwald's conditions is a key reaction to constructing the oxindoline core in the target.

Original languageEnglish
Pages (from-to)183-190
Number of pages8
JournalHeterocycles
Volume76
Issue number1
DOIs
Publication statusPublished - 2008 Dec 1

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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