A Model System for the Synthesis of Complanadine Alkaloids by “Diverted Kondrat’eva” Oxazole–Olefin Cycloaddition

A synthetic approach to complanadine alkaloids is described which employs a Kondrat’eva reaction to construct the pyridine rings. The viability of this approach is demonstrated by its application to a model substrate accessed from unfunctionalized decalin. The key transformation affords the desired...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 78; no. 12; pp. 6253 - 6263
Main Authors Uosis-Martin, Mario, Pantoş, G. Dan, Mahon, Mary F, Lewis, Simon E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.06.2013
Amer Chemical Soc
Subjects
Alkaloids - chemical synthesis
Alkenes - chemistry
Chemistry
Chemistry, Organic
Cycloaddition Reaction
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Molecular Structure
Naphthalenes - chemistry
Oxazoles - chemistry
Physical Sciences
Pyridines - chemistry
Science & Technology
FUNCTIONALIZATION
DBN
(-)-PLECTRODORINE
DIELS-ALDER REACTIONS
NUCLEOPHILIC BEHAVIOR
PYRIDINE SYNTHESIS
DECALIN
LYCOPODIUM ALKALOIDS
CRAFTS ACETYLATING AGENT
C-H ACTIVATION
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Summary:A synthetic approach to complanadine alkaloids is described which employs a Kondrat’eva reaction to construct the pyridine rings. The viability of this approach is demonstrated by its application to a model substrate accessed from unfunctionalized decalin. The key transformation affords the desired tetracyclic architecture with unprecedented incorporation of substituents on the pyridine ring, implicating the oxazole α-hydroxy group as an active participant in the cycloadduct fragmentation process.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401014n