MacKeith R A, McCague R, Olivo H F, Roberts S M, Taylor S J, Xiong H
Department of Chemistry, Exeter University, Devon, U.K.
Bioorg Med Chem. 1994 Jun;2(6):387-94. doi: 10.1016/0968-0896(94)80005-7.
The endo-hydroxylactone (+/-)-(1) was resolved by enantioselective acetylation using Candida cylindracea lipase or preferentially Pseudomonas fluorescens lipase (pfl). Alternatively the corresponding butyrate (+/-)-(3) was hydrolysed with pfl to give the ester (+)-(1S,4R,5S)-(3) and the alcohol (-)-(1R,4S,5R)-(1). The latter compound was converted into carbovir (-)-(1R,4S)-(12) while the ester (+)-(3) was transformed into the delta-lactone (+)-(3R,5S)-(18). The exo-hydroxylactone (+/-)-(2) was resolved less efficiently by a trans-esterification process employing pfl and vinyl acetate.
内消旋羟基内酯（±）-（1）通过使用柱形假丝酵母脂肪酶或优先使用荧光假单胞菌脂肪酶（pfl）进行对映选择性乙酰化来拆分。或者，相应的丁酸酯（±）-（3）用pfl水解，得到酯（+）-（1S，4R，5S）-（3）和醇（-）-（1R，4S，5R）-（1）。后一种化合物转化为卡波韦（-）-（1R，4S）-（12），而酯（+）-（3）转化为δ-内酯（+）-（3R，5S）-（18）。外消旋羟基内酯（±）-（2）通过使用pfl和乙酸乙烯酯的酯交换过程拆分效率较低。
