An alternative approach towards C-12 functionalized scalaranic sesterterpenoids synthesis of 17-Oxo-20-norscalaran-12α,19-O-lactone
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MORĂRESCU (CHETRARU), Olga, GRINCO, Marina, KULCIŢKI, Veaceslav, SHOVA, Sergiu, UNGUR, Nikon. An alternative approach towards C-12 functionalized scalaranic sesterterpenoids synthesis of 17-Oxo-20-norscalaran-12α,19-O-lactone. In: Marine Drugs, 2021, nr. 11(19), pp. 1-9. ISSN 1660-3397. DOI: https://doi.org/10.3390/md19110636
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Marine Drugs
Numărul 11(19) / 2021 / ISSN 1660-3397

An alternative approach towards C-12 functionalized scalaranic sesterterpenoids synthesis of 17-Oxo-20-norscalaran-12α,19-O-lactone

DOI: https://doi.org/10.3390/md19110636

Pag. 1-9

Morărescu (Chetraru) Olga1, Grinco Marina1, Kulciţki Veaceslav1, Shova Sergiu23, Ungur Nikon1
 
1 Institute of Chemistry,
2 Ningbo University,
3 “Petru Poni” Institute of Macromolecular Chemistry
 
Disponibil în IBN: 2 decembrie 2021


Rezumat

Scalarane sesterterpenoids emerged as interesting bioactive natural products which were isolated extensively from marine sponges and shell-less mollusks. Some representatives were also re-ported recently from superior plants. Many scalarane sesterterpenoids displayed a wide spectrum of valuable properties, such as antifeedant, antimicrobial, antifungal, antitubercular, antitumor, anti-HIV properties, cytotoxicity and stimulation of nerve growth factor synthesis, as well as anti-inflammatory activity. Due to their important biological properties, many efforts have been undertaken towards the chemical synthesis of natural scalaranes. The main synthetic challenges are connected to their complex polycyclic framework, chiral centers and different functional groups, in particular the oxygenated functional groups at the C-12 position, which are prerequisites of the biological activity of many investigated scalaranes. The current work addresses this problem and the synthesis of 17-oxo-20-norscalaran-12α,19-O-lactone is described. It was performed via the 12α-hydroxy-ent-isocopal-13(14)-en-15-al obtained from (-)-sclareol as an accessible starting material. The tetracyclic lactone framework was built following an addition strategy, which includes the intramolecular Michael addition of a diterpenic acetoacetic ester and an intramolecular aldol condensation reaction as key synthetic steps. The structure and stereochemistry of the target compound have been proven by X-Ray diffraction method. 

Cuvinte-cheie
Natural terpenoids, Scalarane sesterterpenoids, synthesis, X-ray analysis