Formal total synthesis of (-)-physostigmine

Kaori Asakawa; Naoyoshi Noguchi; Masahisa Nakada

doi:10.3987/COM-08-S(N)29

Formal total synthesis of (-)-physostigmine

Kaori Asakawa, Naoyoshi Noguchi, Masahisa Nakada

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

11 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 language	English
Pages (from-to)	183-190
Number of pages	8
Journal	Heterocycles
Volume	76
Issue number	1
DOIs	https://doi.org/10.3987/COM-08-S(N)29
Publication status	Published - 2008 Dec 1

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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AB - 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.

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Formal total synthesis of (-)-physostigmine

Abstract

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