Stereoselective Synthesis of Novel (±)-trans-Dihydronarciclasine Analogues: Preparation of a Pivotal Intermediate Containing Two Methoxy Substituents
Authors
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Balázs Lévai
Affiliation
Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
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Gábor Varró
Affiliation
Gedeon Richter Plc., Gyömrői út 19-21., H-1103 Budapest, Hungary
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András Simon
Affiliation
Department of Inorganic and Analytical Chemistry, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
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László Hegedűs
AffiliationDepartment of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
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István Kádas
Affiliation
Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
Abstract
An efficient stereoselective synthesis of a pivotal intermediate, a cyclic allyl alcohol derivative containing two methoxy groups [(±)-22], using for the preparation of (±)-trans-dihydronarciclasine analogues was elaborated starting from easily available and inexpensive methyl gallate. This new synthetic route consists of 17 reaction steps, and provides an opportunity to obtain the wanted alkaloid derivative containing an additional methoxy group at position 11, in the ring A of the phenanthridone scaffold.
Keywords:
alkaloids, phenanthridone scaffold, stereoselective synthesisCitation data from Crossref and Scopus
