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7740643 
Journal Article 
Chemoenzymatic synthesis of ((4R,6S)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxinan-4-yl)-acetic acid tert-butyl ester 
Sun Feng-Lai; Wu Jian-Ping; Xu Gang; Yang Li-Rong 
2008 
1 
Youji Huaxue / Chinese Journal of Organic Chemistry
ISSN: 0253-2786 
SCIENCE PRESS 
BEIJING 
28 
6 
1102-1106 
Chinese 
WOS:000257409400025 
A new synthetic method for ((4R,6S)-6-hydroxymethyl-2,2-dimethyl-1,3- dioxinan-4-yl)-acetic acid tert-butyl ester was accomplished by a chemoenzymatic approach. Racemic 4-(4-methylbenzyloxy)-3-hydroxybutyronitrile (3) was firstly synthesized via condensation and epoxy opening reactions. (S)-4-(4- Methylbenzyloxy)-3-hydroxybutyronitrile (4) was obtained from resolution of racemic 3 by the lipase from Artgribacter sp. with a high enantiomeric excess (98% ee) in the mixture solvent of acetonitrile/hexane (V : V= 1 : 4). Dihydroxy ester 7 was synthesized by a syn-selective triethylborane mediated reduction with a de value of 97%. After acid-catalyzed protection of 7 and hydrogenolysis of the benzyl protecting group, the objective 9 was obtained with a high optical purity. 
statins; chemoenzymic synthesis; enzymatic resolution; triethylborane