Evaluation of lipases in the desymmetrization of meso-exo-3,5-dihydroxymethylenetricyclo[5.2.1.0(2,6)]decane and the synthesis of chiral derivatives

Abstract

A dessimetrização mais eficiente do composto meso- exo-3,5-dihidroximetilenotriciclo[5.2.1.0 2,6 ]decano foi com a lipase da Pseudomonas cepacia (PS-C 'Amano' II) em acetato de vinila, quando obteve-se alto rendimento químico (93%) e excelente excesso enantiomérico (ee ≥ 99%), determinado por cromatografia gasosa em coluna quiral. Desse sistema quiral, foram preparados derivados enantiopuros com potenciais aplicações como intermediários sintéticos. -exo-3,5-dihydroxymethylenetricyclo[5.2.1.0 2,6 ]decane was efficiently desymmetrized by the lipase from Pseudomonas cepacia (PS-C 'Amano' II) in vinyl acetate in high yields (93%) and with excellent enantiomeric excesses (ee ≥ 99% by chiral GC). Chiral synthons for asymmetric synthesis were synthesized from this enantiopure compound. meso

3,4-Seco-12α-hydroxy-5β-cholan-3,4,24-trioic Acid, a Novel Secondary Bile Acid: Isolation from the Bile of the Common Ringtail Possum (Pseudocheirus peregrinus) and Chemical Synthesis

“…Oxidative cleavage of compound 2 with sodium periodate [11,12] and subsequent treatment of the resulting product with Jones reagent resulted in simultaneous dicarboxylation at C-3 and C-4 to give 3,4-seco-12α-acetoxy-5β-cholan-3,4,24-trioic acid 24-methyl ester (3). Alkaline hydrolysis of the 3 followed by acidification afforded the desired 3,4,24-trioic acid (1).…”