Synthetic Studies on Quinine:  Quinuclidine Construction via a Ketone Enolate Regio- and Diastereoselective Pd-Mediated Allylic Alkylation

7-Hydroxy-quinine was synthesized by an asymmetric aldol reaction that establishes the C8 and C9 stereochemistry, followed by construction of the 3-vinyl-quinuclidine azabicyclo[2.2.2]octane by C3−C4 ring closure using an intramolecular palladium-mediated allylic alkylation with excellent regio- and...

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Bibliographic Details
Published inOrganic letters Vol. 8; no. 18; pp. 4051 - 4054
Main Authors Johns, Deidre M, Mori, Makoto, Williams, Robert M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.08.2006
Amer Chemical Soc
Subjects
Alkylation
Catalysis
Chemistry
Chemistry, Organic
Ketones - chemistry
Molecular Structure
Palladium - chemistry
Physical Sciences
Quinine - chemistry
Quinuclidines - chemical synthesis
Science & Technology
PALLADIUM
ANALOGS
CYCLIZATION
STEREOCONTROLLED TOTAL-SYNTHESIS
ALKALOIDS
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Summary:7-Hydroxy-quinine was synthesized by an asymmetric aldol reaction that establishes the C8 and C9 stereochemistry, followed by construction of the 3-vinyl-quinuclidine azabicyclo[2.2.2]octane by C3−C4 ring closure using an intramolecular palladium-mediated allylic alkylation with excellent regio- and diastereoselectivity. This is the first report of a ketone-enolate-stereocontrolled allylic alkylation mediated by palladium. The title compound and a dehydro-quinine analogue were evaluated for antimalarial activity.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol061524s