Synthesis of a C12-functionalized norscalarane from sclareol
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2023-06-10 11:23
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MORĂRESCU (CHETRARU), Olga, GRINCO, Marina, KULCIŢKI, Veaceslav, UNGUR, Nikon. Synthesis of a C12-functionalized norscalarane from sclareol. In: Achievements and perspectives of modern chemistry, 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 230. ISBN 978-9975-62-428-2.
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Achievements and perspectives of modern chemistry 2019
Conferința "International Conference "Achievements and perspectives of modern chemistry""
Chişinău, Moldova, 9-11 octombrie 2019

Synthesis of a C12-functionalized norscalarane from sclareol


Pag. 230-230

Morărescu (Chetraru) Olga, Grinco Marina, Kulciţki Veaceslav, Ungur Nikon
 
Institute of Chemistry
 
Disponibil în IBN: 12 noiembrie 2019


Rezumat

Scalarane sesterterpenoids emerged as interesting bioactive natural products which have been isolated basically from marine sponges and shell-less mollusks [1]. Some representatives isolated from plants are also known [2,3]. A range of scalarane sesterterpenoids displayed a wide spectrum of interesting biological properties, such as antifeedant, antimicrobial, antifungal, antitubercular, antitumor, cytotoxicity, anti-HIV, stimulation of nerve growth factor synthesis, as well as anti-inflammatory activity [1,3,4]. Due to their important biological properties, many efforts have been undertaken for the construction of this framework [5-7]. The main synthetic difficulty lies in their challenging structures, many chiral centers and different functional groups attached, especially the oxygenated functional group at the C12 position that is a prerequisite for the biological activity of many investigated scalaranes. The current work is dedicated to solving this problem. The synthesis of C12-functionalized norscalarane was performed via an isocopalic derivative using (-)-sclareol as accessible starting material (Scheme). The tetracyclic lactone framework was build following an addition strategy, which includes intramolecular Michael reaction of a tricyclic acetoacetic ester derivative and intramolecular aldol condensation as key synthetic steps.formula