Concise Synthesis of Both Enantiomers of Pilocarpine
Theresa Schmidt,
Niels Heise,
Kurt Merzweiler,
Hans-Peter Deigner,
Ahmed Al-Harrasi,
René Csuk
Affiliations
Theresa Schmidt
Department of Organic Chemistry, Martin-Luther University Halle-Wittenberg, Kurt-Mothes Str. 2, D-06120 Halle (Saale), Germany
Niels Heise
Department of Organic Chemistry, Martin-Luther University Halle-Wittenberg, Kurt-Mothes Str. 2, D-06120 Halle (Saale), Germany
Kurt Merzweiler
Department of Inorganic Chemistry, Martin-Luther University Halle-Wittenberg, Kurt-Mothes Str. 2, D-06120 Halle (Saale), Germany
Hans-Peter Deigner
Medical and Life Science Faculty, Institute of Precision Medicine, Furtwangen University, Jakob-Kienzle, Str. 17, D-78054 Villingen–Schwenningen, Germany
Ahmed Al-Harrasi
Chair of Oman’s Medicinal Plants and Marine Natural Products, University of Nizwa, P.O. Box 33, PC 616 Nizwa, Oman
René Csuk
Department of Organic Chemistry, Martin-Luther University Halle-Wittenberg, Kurt-Mothes Str. 2, D-06120 Halle (Saale), Germany
Furan-2-carboxylic acid was used as a starting material for the synthesis of dehydro-homopilopic acid. Esterification, hydrogenation and enzymatic hydrolysis followed by the reduction of Weinreb amides and a single-step attachment of a 1-methyl-imidazole residue allowed for the concise synthesis of both enantiomers of pilocarpine.