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Cyclocholates with 12‐Oxo and 7,12‐Oxo Groups
Author(s) -
Gao Hongwu,
Dias Jerry Ray
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199804)1998:4<719::aid-ejoc719>3.0.co;2-f
Subject(s) - cholic acid , chemistry , carboxylic acid , stereochemistry , group (periodic table) , bile acid , organic chemistry , biochemistry
Syntheses of bile acid cyclooligomers with 12‐ and 7,12‐oxo groups ( 6a−d , 7a−c , 8a−b ) by the Yamaguchi method are described. Cyclotrimerization is the principal reaction route for these cholic acid systems. Conversion of 7‐ and 12‐hydroxy groups in cholic acid ( 1a−b ) to oxo groups ( 4a−c , 5a−c ), followed by macrocyclization ( 6a−d , 7a−c , 8a−b ) and selective reduction of the oxo groups back to hydroxy ones without cleaving the 24‐carboxylic ester linkages ( 11 ) constitutes a new strategy in the synthesis of cyclocholates having unprotected hydroxy groups.