Synthesis of 3α,12α-dihydroxy-23a, 23b-dihomo-5β-cholan-24-oic acid | Zendy

Vera Ćirin-Novta | Zendy; Ksenija Kuhajda | Zendy; Julijan Kandrač | Zendy; S. Kevrešan | Zendy

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Synthesis of 3α,12α-dihydroxy-23a, 23b-dihomo-5β-cholan-24-oic acid

Author(s) -

Vera Ćirin-Novta,

Ksenija Kuhajda,

Julijan Kandrač,

S. Kevrešan

Publication year - 2004

Publication title -

journal of the serbian chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.227

H-Index - 45

eISSN - 1820-7421

pISSN - 0352-5139

DOI - 10.2298/jsc0405349c

Subject(s) - chemistry , yield (engineering) , decarboxylation , derivative (finance) , hydrolysis , alcohol , medicinal chemistry , tosyl , sodium , ether , organic chemistry , catalysis , materials science , economics , financial economics , metallurgy

A novel multi-step synthesis of 3α,12α-dihydroxy-23a,23b-dihomo-5β-cholan-24-oic acid (23a,23b-dihomodeoxycholic acid) (5) has been achieved from methyl 3α,12α-dihydroxy-5β-cholanoate (1). Reduction of compound 1 with LiAlH 4 in dry ether gave the corresponding alcohol 2 in 83 % yield. Selective esterification of compound 2 with tosyl chloride in dry piridine at 0-5 °C for 12 h afforded the 3α,12α-dihydroxy-5β-24-cholanyl tosylate (3) in 64 % yield. The reaction of the tosyl derivative 3 with sodium diethyl malonate gave compound 4 which was first subjected to hydrolysis under basic conditions, followed by decarboxylation under acidic conditions to afford 3α,12α-dihydroxy-5β-23a,23b-dihomocholan-24-oic acid in 84 % yield.

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