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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2010

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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.

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Other article

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garsubellin-a, bridgehead lithiation, clusianone, (+/-)-clusianone, ketones, benzophenones, derivatives, nemorosone, chemistry, organic

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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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https://hdl.handle.net/10161/4109

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10.1021/ol1022728

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