Conjugate Addition of Lithiated Methyl Pyridines to Enones

Preparatively useful conjugate addition of lithiated methyl pyridines to cyclic and acyclic enones is reported. Addition of 2-picoline to 3-penten-2-one led to a concise synthesis of the alkaloids (±)-senepodine G and (±)-cermizine C.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 75; no. 16; pp. 5737 - 5739
Main Authors Taber, Douglass F, Guo, Pengfei, Pirnot, Michael T
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.08.2010
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyclopentanes - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic Compounds, 2-Ring - chemical synthesis
Heterocyclic Compounds, 2-Ring - chemistry
Molecular Structure
Organic chemistry
Physical Sciences
Picolines - chemistry
Preparations and properties
Science & Technology
Stereoisomerism
TROPANE ALKALOIDS
PYRROLIDINE
PIPERIDINE
LYCOPODIUM
CERNUANE-TYPE
Alkaloid
Lithium Organic compounds
Quinolizine derivatives
Cyclic compound
Nitrogen heterocycle
Addition reaction
Chemical synthesis
Enone
Picolines
Pyridine derivatives
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Summary:Preparatively useful conjugate addition of lithiated methyl pyridines to cyclic and acyclic enones is reported. Addition of 2-picoline to 3-penten-2-one led to a concise synthesis of the alkaloids (±)-senepodine G and (±)-cermizine C.
Bibliography:NIH RePORTER
ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo100890s