Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D
Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D
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DOI：
10.1021/jo9519569
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发表时间：
1996-05-17
影响因子：
3.6
通讯作者：
Dickman, M
中科院分区：
文献类型：
--
作者：
Chenevert, R;Dickman, M
哌啶基化合物是植物、昆虫和两栖动物中发现的一类重要的天然生物碱。通过黑曲霉脂肪酶 (ANL) 酶促去对称化内消旋顺式 2,6- 和顺式,顺式-2,4,6 取代哌啶，提出了 2-烷基-6-甲基哌啶的一般不对称合成。酶促反应以优异的化学产率和高对映体选择性（ee 大于或等于 98%）进行。该通用方法用于合成(+)-二氢蒎啶-HCl以及首次不对称合成石斛酸生物碱(+)-241D。
Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase(ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee greater than or equal to 98%). The general method is used to effect the synthesis of (+)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.