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Latvian Institute of Organic Synthesis, Latvia
Posters & Accepted Abstracts: Organic Chem Curr Res
β-Caryophyllene is one of the most accessible sesquiterpenes found in nature and it is available at low price from several commercial sources. The bicyclic structure of β-caryophyllene with condensed gemdimethylcyclobutane and E-cyclononene rings combined with two stereodefined chiral centers render this terpene as an attractive renewable source to access diverse high value compounds. The study of chemoselective transformations of β-caryophyllene opened an opportunity to develop a concise semisynthetic route towards biologically active sesquiterpene lactones (rumphellaones A-C and their C-8 epimers). Rumphellaones A-C are 4,5-seco-carryophyllane sesquiterpenoids which were isolated from the gorgonian coral Rumphella antipathies and display cytotoxicity toward human T-cell lymphoblastic leukemia as well as inhibit the generation of superoxide anions and the release of elastase by human neutrophils. Rumphellaone A was synthesized in the shortest reaction sequence reported whereas rumphellaones B and C were obtained for the first time by chemical synthesis. Absolute configuration of final products was unambiguously confirmed by single crystal X-ray analysis.
Georgijs Stakanovs has received his B.Sc. and M.Sc. at Riga Technical University and currently is a PhD student and a research assistant in Latvian Institute of Organic Synthesis. He is a co-author of 3 papers covering topics of novel potential malaria plasmepsin inhibitors as well as development of semisynthesis of natural products.