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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

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Date
2010
Authors
Garnsey, Michelle R
Lim, Daniel
Yost, Julianne M
Coltart, Don M
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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.
Type
Other article
Subject
garsubellin-a
bridgehead lithiation
clusianone
(+/-)-clusianone
ketones
benzophenones
derivatives
nemorosone
chemistry, organic
Permalink
https://hdl.handle.net/10161/4109
Published Version (Please cite this version)
10.1021/ol1022728
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.
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