Asymmetric total synthesis of (+)- and (-)-clusianone and (+)- and (-)-clusianone methyl enol ether via ACC alkylation and evaluation of their anti-HIV activity |
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| Authors: | Garnsey Michelle R Matous James A Kwiek Jesse J Coltart Don M |
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| Institution: | a Department of Chemistry, Duke University, Durham, NC 27705, USA
b Department of Microbiology and the Division of Infectious Diseases, The Ohio State University, Columbus, Ohio 43210, USA |
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| Abstract: | The total asymmetric synthesis of (+)- and (−)-clusianone and (+)- and (−)-clusianone methyl enol ether is reported. Asymmetric induction is achieved through the use of ACC alkylation, providing the key intermediates with an er of 99:1. The four synthetic compounds were evaluated for their anti-HIV activity. Both (+)- and (−)-clusianone displayed significant anti-HIV activity. |
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| Keywords: | ACC alkylation Asymmetric synthesis Polycyclic polyprenylated acylphloroglucinols Viral infection Anti-HIV activity |
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