Development of a Strategy for the Asymmetric Synthesis of Polycyclic Polyprenylated Acylphloroglucinols via N-Amino Cyclic Carbamate Hydrazones: Application to the Total Synthesis of (+)-Clusianone

A broadly applicable asymmetric synthetic strategy utilizing N-amino cyclic carbamate alkylation that provides access to the various stereochemical permutations of a common structural motif found in many polycyclic polyprenylated acylphloroglucinols is described. The utility of this methodology is d...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 22; pp. 5234 - 5237
Main Authors Garnsey, Michelle R, Lim, Daniel, Yost, Julianne M, Coltart, Don M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.11.2010
Amer Chemical Soc
Subjects
Alkylation
Antiviral Agents - chemical synthesis
Antiviral Agents - chemistry
Antiviral Agents - pharmacology
Benzophenones
Benzoquinones
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Bridged Bicyclo Compounds - pharmacology
Carbamates
Chemistry
Chemistry, Organic
Hydrazones - chemistry
Molecular Structure
Phloroglucinol - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
KETONES
(+/-)-CLUSIANONE
BRIDGEHEAD LITHIATION
CLUSIANONE
BENZOPHENONES
DERIVATIVES
GARSUBELLIN-A
NEMOROSONE
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Summary:A broadly applicable asymmetric synthetic strategy utilizing N-amino cyclic carbamate alkylation that provides access to the various stereochemical permutations of a common structural motif found in many polycyclic polyprenylated acylphloroglucinols is described. The utility of this methodology is demonstrated through the first asymmetric total synthesis of the antiviral agent (+)-clusianone.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1022728