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Total Synthesis of Mesembrine – The Construction of Quaternary Stereocenters by Gold‐Catalyzed Diyne Desymmetrization
Author(s) -
Czekelius Constantin
Publication year - 2018
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201700060
Subject(s) - desymmetrization , stereocenter , chemistry , enantioselective synthesis , catalysis , context (archaeology) , methylene , organic chemistry , stereochemistry , total synthesis , combinatorial chemistry , paleontology , biology
This review gives an overview on synthetic methodology developed for the synthesis of the naturally occurring alkaloid mesembrine. Its all‐carbon‐substituted quaternary stereocenter has fuelled creativity in the application of ex‐chiral‐pool‐synthesis , chiral auxiliaries, and asymmetric catalysis alike. The gold‐catalyzed desymmetrization of 1,4‐diynes has been demonstrated as a selective method for the enantioselective preparation of methylene pyrrolidines incorporating a quaternary stereocenter. The applicability of this method has therefore been demonstrated in the context of a mesembrine total synthesis.