A convenient synthesis of 5beta-cholestan-26-oic and 5beta-cholestan-26,27-dioic acids.
A new method for the preparation of 5beta-cholestan-26-oic acids 7 and their analogs is described. The key steps in the synthesis are: iodination of bis- and tris-formyloxy-5beta-cholan-24-ols 3; nucleophilic substitution of iodides 4 with diethyl sodiomalonate; complete alkaline hydrolysis of esters 5; and subsequent decarboxylation of geminal diacids 6 in DMSO.
Starchenkov
I
I
Latvian Institute of Organic Synthesis, Aizkraukles iela 21, Riga, Latvia.
Trapencieris
P
P
Kauss
V
V
Jas
G
G
Kalvinsh
I
I
D002777:Cholestanols / Q000138:chemical synthesis*
C406714:3,7,12-trihydroxy-25-carboxycholestan-26-oic acid; C406715:3,7,12-trihydroxycholestan-26,27-dioic acid; C000986:3,7-dihydroxycholestan-26-oic acid; D002777:Cholestanols; C022069:3,7,12-trihydroxycholestan-26-oic acid