Synthesis of 3α,12α-dihydroxy-23a, 23b-dihomo-5β-cholan-24-oic acid
| Autor: | Ćirin-Novta Vera S., Kuhajda Ksenija N., Kandrač Julijan E., Kevrešan Slavko E. |
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| Jazyk: | angličtina |
| Rok vydání: | 2004 |
| Předmět: | |
| Zdroj: | Journal of the Serbian Chemical Society, Vol 69, Iss 5, Pp 349-351 (2004) |
| Druh dokumentu: | article |
| ISSN: | 0352-5139 1820-7421 |
| DOI: | 10.2298/JSC0405349C |
| Popis: | 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 LiAlH4 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 ºC 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. |
| Databáze: | Directory of Open Access Journals |
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