Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom