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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

dc.contributor.author Garnsey, Michelle R
dc.contributor.author Lim, Daniel
dc.contributor.author Yost, Julianne M
dc.contributor.author Coltart, Don M
dc.date.accessioned 2011-06-21T17:27:11Z
dc.date.available 2011-06-21T17:27:11Z
dc.date.issued 2010
dc.identifier.citation Garnsey,Michelle R.;Lim,Daniel;Yost,Julianne M.;Coltart,Don M.. 2010. 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. Organic letters 12(22): 5234-5237.
dc.identifier.issn 1523-7060
dc.identifier.uri https://hdl.handle.net/10161/4109
dc.description.abstract 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.
dc.language.iso en_US
dc.publisher American Chemical Society (ACS)
dc.relation.isversionof 10.1021/ol1022728
dc.subject garsubellin-a
dc.subject bridgehead lithiation
dc.subject clusianone
dc.subject (+/-)-clusianone
dc.subject ketones
dc.subject benzophenones
dc.subject derivatives
dc.subject nemorosone
dc.subject chemistry, organic
dc.title 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
dc.title.alternative
dc.type Other article
dc.description.version Version of Record
duke.date.pubdate 2010-11-19
duke.description.issue 22
duke.description.volume 12
dc.relation.journal Organic letters
pubs.begin-page 5234
pubs.end-page 5237


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