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

Bioorganic & Medicinal Chemistry Letters
2011.0

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.

Knowledge Graph

Similar Paper

Asymmetric total synthesis of (+)- and (−)-clusianone and (+)- and (−)-clusianone methyl enol ether via ACC alkylation and evaluation of their anti-HIV activity
Bioorganic & Medicinal Chemistry Letters 2011.0
Clausanisumine, a Prenylated Bicarbazole Alkaloid from the Fruits of Clausena anisum-olens and Its Potential Anti-HIV Activity
The Journal of Organic Chemistry 2021.0
Carbazole Alkaloids from Clausena anisum-olens: Isolation, Characterization, and Anti-HIV Evaluation
Molecules 2019.0
Synthesis, Chromatographic Resolution, and Anti-Human Immunodeficiency Virus Activity of (±)-Calanolide A and Its Enantiomers
Journal of Medicinal Chemistry 1996.0
Bioactive constituents of Clausena lansium and a method for discrimination of aldose enantiomers
Phytochemistry 2012.0
Synthesis and anti-HIV activity of oleanolic acid derivatives
Bioorganic & Medicinal Chemistry Letters 2001.0
Anti-AIDS Agents, 11. Betulinic Acid and Platanic Acid as Anti-HIV Principles from Syzigium claviflorum, and the Anti-HIV Activity of Structurally Related Triterpenoids
Journal of Natural Products 1994.0
Total Synthesis of Cladoniamide G
Organic Letters 2013.0
Anti-aids agents 33.1 Synthesis and anti-HIV activity of mono-methyl substituted 3′,4′-di-O-(−)-camphanoyl-(+)-cis-khellactone (DCK) analogues
Bioorganic & Medicinal Chemistry Letters 1998.0
Total synthesis and in vitro bioevaluation of clavaminols A, C, H & deacetyl clavaminol H as potential chemotherapeutic and antibiofilm agents
European Journal of Medicinal Chemistry 2016.0