Effects of shape oil thermodynamic cyclizations of cinchona alkaloids

Thermodynamic cyclizations of a series of cinchona alkaloid derivatives are investigated. An extended quinine monomer 2:HO-Ce-OMe is prepared and cyclized to produce a mixture of cyclic oligomers. Combining the extended monomer 2:HO-Ce-OMe with the previously reported cinchonidine monomer 1b:HO-Cc-O...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 64; no. 16; pp. 5804 - 5814
Main Authors Rowan, SJ, Reynolds, DJ, Sanders, JKM
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 06.08.1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MACROCYCLES
COMBINATORIAL LIBRARIES
RECEPTOR
SYSTEMS
GENERATION
DIVERSITY
SELECTION
COMBINED NMR
Online AccessGet full text

Cover

More Information
Summary:Thermodynamic cyclizations of a series of cinchona alkaloid derivatives are investigated. An extended quinine monomer 2:HO-Ce-OMe is prepared and cyclized to produce a mixture of cyclic oligomers. Combining the extended monomer 2:HO-Ce-OMe with the previously reported cinchonidine monomer 1b:HO-Cc-OMe under thermodynamic control produces a library of quinine-derived macrocycles. Two quinidine-derived methyl ester monomers 10:HO-Cd-OMe and 16:HO-Ca-OMe are also reported. Both are preorganized to form cyclic dimers; upon carrying out the thermodynamic cyclization on a mixture of both monomers only a small percentage (5%) of the hetero-dimer is obtained. Thermodynamic cyclization of the corresponding cinchonidine derived methyl ester 1b:HO-Cc-OMe with 10:HO-Cd-OMe results in the self-sorting of the two diastereoisomers.
ISSN:0022-3263
DOI:10.1021/jo982496x