Formal total synthesis of (-)-physostigmine

Kaori Asakawa, Naoyoshi Noguchi, Masahisa Nakada

    Research output: Contribution to journal › Article

    9 Citations (Scopus)

    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

    Fingerprint

    Physostigmine
    Esters
    Esterases
    Liver
    Hydrolysis
    Swine
    Acids
    malonic acid

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Organic Chemistry
    • Pharmacology

    Cite this

    Formal total synthesis of (-)-physostigmine. / Asakawa, Kaori; Noguchi, Naoyoshi; Nakada, Masahisa.

    In: Heterocycles, Vol. 76, No. 1, 2008, p. 183-190.

    Research output: Contribution to journal › Article

    Asakawa, K, Noguchi, N & Nakada, M 2008, 'Formal total synthesis of (-)-physostigmine', Heterocycles, vol. 76, no. 1, pp. 183-190. https://doi.org/10.3987/COM-08-S(N)29
    Asakawa K, Noguchi N, Nakada M. Formal total synthesis of (-)-physostigmine. Heterocycles. 2008;76(1):183-190. https://doi.org/10.3987/COM-08-S(N)29
    Asakawa, Kaori ; Noguchi, Naoyoshi ; Nakada, Masahisa. / Formal total synthesis of (-)-physostigmine. In: Heterocycles. 2008 ; Vol. 76, No. 1. pp. 183-190.
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