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Asymmetric total synthesis of (+)- and (-)-clusianone and (+)- and (-)-clusianone methyl enol ether via ACC alkylation and evaluation of their anti-HIV activity.

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.

SUBMITTER: Garnsey MR

PROVIDER: S-EPMC3070777 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Asymmetric total synthesis of (+)- and (-)-clusianone and (+)- and (-)-clusianone methyl enol ether via ACC alkylation and evaluation of their anti-HIV activity.

Garnsey Michelle R MR Matous James A JA Kwiek Jesse J JJ Coltart Don M DM

Bioorganic & medicinal chemistry letters 20110223 8

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. ...[more]

PMID: 21414776

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