Enzymatic Route to Chiral, Nonracemic cis-2,6- and cis,cis-2,4,6-Substituted Piperidines. Synthesis of (+)-Dihydropinidine and Dendrobate Alkaloid (+)-241D

Autor:	Robert Chênevert, Michael Dickman
Rok vydání:	1996
Předmět:	chemistry.chemical_classification Stereochemistry Alkaloid fungi Organic Chemistry Enantioselective synthesis Dendrobate alkaloid 241D Desymmetrization chemistry.chemical_compound Enzyme chemistry Yield (chemistry) Piperidine Selectivity
Zdroj:	The Journal of Organic Chemistry. 61:3332-3341
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo9519569
Popis:	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 ≥ 98%). The general method is used to effect the synthesis of (+)-dihydropinidine−HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.
Databáze:	OpenAIRE
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