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Structure‐Directed Synthesis under Thermodynamic Control: Macrocyclic Trimers from Cinchona Alkaloids
Author(s) -
Rowan Stuart J.,
Brady Paul A.,
Sanders Jeremy K. M.
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199621431
Subject(s) - trimer , cinchonidine , yield (engineering) , cinchona alkaloids , chemistry , cinchona , quinine , organic chemistry , stereochemistry , enantioselective synthesis , catalysis , materials science , dimer , malaria , immunology , metallurgy , biology
A remarkably narrow product distribution is observed in the thermodynamic cyclization of modified Cinchona alkaloids to yield predominantly the trimer 1 (X = H, OMe); this is a representative of a new class of macrocycle. The reaction was proved to be reversible by resubmitting the cinchonidine (X = H) and quinine (X = OMe) to the reaction conditions: a statistical mixture of all four possible trimers was obtained.