β-Caryophyllene in divergent semisynthesis of rumphellaones A- | 59390
Organic Chemistry: Current Research

Organic Chemistry: Current Research
Open Access

ISSN: 2161-0401

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β-Caryophyllene in divergent semisynthesis of rumphellaones A-C

Joint Meet on Euro Chemistry 2021 & Natural Products 2021 & Pharmaceutical Sciences 2021

June 21-22, 2021 | WEBINAR

Georgijs Stakanovs

Latvian Institute of Organic Synthesis, Latvia

Posters & Accepted Abstracts: Organic Chem Curr Res

Abstract :

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.

Biography :

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.