The invention relates to a process for prepg. a compd. I in particular obeticholic acid (II) and intermediates suitable for its synthesis. A process for the prepn. of II comprises the use of hyodeoxycholic acid (III) as the starting material, Wittig reaction of oxocholate IV [wherein; Ra is H or an (un)substituted linear or branched C1-6-alkyl, or an (un)substituted aryl; Rb is H; and, Rc is OH or O-PG; wherein PG is an alc. protecting group;]. [Or, Rb is OR1 and Rc is OR2; wherein each of R1 and R2, which are the same or different, is a C1-6-alkyl group; or, R1 and R2 taken together form a (CH2)n chain; wherein n is 2 or 3,] with EtPh3P+Br-;allylic oxidn. of ethylidenechenodeoxycholate V; and hydrogenation, stereoselective redn. and sapon. of ethyldioxocholate VI.
Method for preparing a farnesoid X receptor agonist obeticholic acid from hyodeoxycholic acid
IULIANO, ANNA;
2017-01-01
Abstract
The invention relates to a process for prepg. a compd. I in particular obeticholic acid (II) and intermediates suitable for its synthesis. A process for the prepn. of II comprises the use of hyodeoxycholic acid (III) as the starting material, Wittig reaction of oxocholate IV [wherein; Ra is H or an (un)substituted linear or branched C1-6-alkyl, or an (un)substituted aryl; Rb is H; and, Rc is OH or O-PG; wherein PG is an alc. protecting group;]. [Or, Rb is OR1 and Rc is OR2; wherein each of R1 and R2, which are the same or different, is a C1-6-alkyl group; or, R1 and R2 taken together form a (CH2)n chain; wherein n is 2 or 3,] with EtPh3P+Br-;allylic oxidn. of ethylidenechenodeoxycholate V; and hydrogenation, stereoselective redn. and sapon. of ethyldioxocholate VI.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
