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^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

13 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

Access to Document

10.3987/COM-08-S(N)29

Cite this

@article{3378f5f4ba67489781f97fcf38da6b7a,

title = "Formal total synthesis of (-)-physostigmine",

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.",

author = "Kaori Asakawa and Naoyoshi Noguchi and Masahisa Nakada",

year = "2008",

month = dec,

day = "1",

doi = "10.3987/COM-08-S(N)29",

language = "English",

volume = "76",

pages = "183--190",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "1",

}

TY - JOUR

T1 - Formal total synthesis of (-)-physostigmine

AU - Asakawa, Kaori

AU - Noguchi, Naoyoshi

AU - Nakada, Masahisa

PY - 2008/12/1

Y1 - 2008/12/1

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=54849436263&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=54849436263&partnerID=8YFLogxK

U2 - 10.3987/COM-08-S(N)29

DO - 10.3987/COM-08-S(N)29

M3 - Article

AN - SCOPUS:54849436263

VL - 76

SP - 183

EP - 190

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 1

ER -

Formal total synthesis of (-)-physostigmine

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this