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Communication | Special issue | Vol 76, No. 1, 2008, pp.183-190
Published online, 8th April, 2008
DOI: 10.3987/COM-08-S(N)29
Formal Total Synthesis of (—)-Physostigmine

Kaori Asakawa, Naoyoshi Noguchi, and Masahisa Nakada*

*Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan


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.