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 demonstrated through the first asymmetric total synthesis of the antiviral agent (+)-clusianone.
Garnsey
Michelle R
MR
Department of Chemistry, Duke University, Durham, North Carolina 27708, United States.
Lim
Daniel
D
Yost
Julianne M
JM
Coltart
Don M
DM
D000478:Alkylation; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002219:Carbamates; D006835:Hydrazones / Q000737:chemistry; D015394:Molecular Structure; D010696:Phloroglucinol / Q000737:chemistry; D013237:Stereoisomerism
C118110:7-epiclusianone; D000998:Antiviral Agents; D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds; D002219:Carbamates; D006835:Hydrazones; D010696:Phloroglucinol