A Simple Enantioselective Route to Functionalized Indolizidines: Synthesis of (+)-Ipalbidine and (+)-Antofine

Autor:	Rajendar Dyapa, Sunil V. Pansare, Rajinikanth Lingampally
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Ketone Indolizidines Organic Chemistry Enantioselective synthesis Nitro compound Indolizidine chemistry.chemical_compound chemistry Organocatalysis Nitro Michael reaction Organic chemistry Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2011:2235-2238
ISSN:	1434-193X
DOI:	10.1002/ejoc.201100125
Popis:	An efficient route to functionalized indolizidines from an enantiomerically enriched γ-nitro ketone is described. The nitro ketone is obtained by an organocatalytic, enantioselective ketone-nitro alkene Michael addition. Oxidative ring expansion of the nitro ketone and subsequent methanolysis provides a 8-nitro-4-oxooctanoate. This is stereoselectively transformed to the key, functionalized indolizidine intermediate which is readily converted to (+)-ipalbidine and (+)-antofine.
Databáze:	OpenAIRE
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