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
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 articleSubject
garsubellin-abridgehead lithiation
clusianone
(+/-)-clusianone
ketones
benzophenones
derivatives
nemorosone
chemistry, organic
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https://hdl.handle.net/10161/4109Published Version (Please cite this version)
10.1021/ol1022728Citation
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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