An Alternative Approach towards C-12 Functionalized Scalaranic Sesterterpenoids Synthesis of 17-Oxo-20-norscalaran-12α,19-<i>O</i>-lactone

Scalarane sesterterpenoids emerged as interesting bioactive natural products which were isolated extensively from marine sponges and shell-less mollusks. Some representatives were also reported recently from superior plants. Many scalarane sesterterpenoids displayed a wide spectrum of valuable prope...

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Autores principales:	Olga Morarescu, Marina Grinco, Veaceslav Kulciţki, Sergiu Shova, Nicon Ungur
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	scalarane sesterterpenoids synthesis natural terpenoids X-ray analysis Biology (General) QH301-705.5
Acceso en línea:	https://doaj.org/article/22c9071ad0a54a288f90c455743d6243
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spelling	oai:doaj.org-article:22c9071ad0a54a288f90c455743d62432021-11-25T18:12:58ZAn Alternative Approach towards C-12 Functionalized Scalaranic Sesterterpenoids Synthesis of 17-Oxo-20-norscalaran-12α,19-<i>O</i>-lactone10.3390/md191106361660-3397https://doaj.org/article/22c9071ad0a54a288f90c455743d62432021-11-01T00:00:00Zhttps://www.mdpi.com/1660-3397/19/11/636https://doaj.org/toc/1660-3397Scalarane sesterterpenoids emerged as interesting bioactive natural products which were isolated extensively from marine sponges and shell-less mollusks. Some representatives were also reported 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-<i>O</i>-lactone is described. It was performed via the 12α-hydroxy-<i>ent</i>-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.Olga MorarescuMarina GrincoVeaceslav KulciţkiSergiu ShovaNicon UngurMDPI AGarticlescalarane sesterterpenoidssynthesisnatural terpenoidsX-ray analysisBiology (General)QH301-705.5ENMarine Drugs, Vol 19, Iss 636, p 636 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	scalarane sesterterpenoids synthesis natural terpenoids X-ray analysis Biology (General) QH301-705.5
spellingShingle	scalarane sesterterpenoids synthesis natural terpenoids X-ray analysis Biology (General) QH301-705.5 Olga Morarescu Marina Grinco Veaceslav Kulciţki Sergiu Shova Nicon Ungur An Alternative Approach towards C-12 Functionalized Scalaranic Sesterterpenoids Synthesis of 17-Oxo-20-norscalaran-12α,19-<i>O</i>-lactone
description	Scalarane sesterterpenoids emerged as interesting bioactive natural products which were isolated extensively from marine sponges and shell-less mollusks. Some representatives were also reported 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-<i>O</i>-lactone is described. It was performed via the 12α-hydroxy-<i>ent</i>-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.
format	article
author	Olga Morarescu Marina Grinco Veaceslav Kulciţki Sergiu Shova Nicon Ungur
author_facet	Olga Morarescu Marina Grinco Veaceslav Kulciţki Sergiu Shova Nicon Ungur
author_sort	Olga Morarescu
title	An Alternative Approach towards C-12 Functionalized Scalaranic Sesterterpenoids Synthesis of 17-Oxo-20-norscalaran-12α,19-<i>O</i>-lactone
title_short	An Alternative Approach towards C-12 Functionalized Scalaranic Sesterterpenoids Synthesis of 17-Oxo-20-norscalaran-12α,19-<i>O</i>-lactone
title_full	An Alternative Approach towards C-12 Functionalized Scalaranic Sesterterpenoids Synthesis of 17-Oxo-20-norscalaran-12α,19-<i>O</i>-lactone
title_fullStr	An Alternative Approach towards C-12 Functionalized Scalaranic Sesterterpenoids Synthesis of 17-Oxo-20-norscalaran-12α,19-<i>O</i>-lactone
title_full_unstemmed	An Alternative Approach towards C-12 Functionalized Scalaranic Sesterterpenoids Synthesis of 17-Oxo-20-norscalaran-12α,19-<i>O</i>-lactone
title_sort	alternative approach towards c-12 functionalized scalaranic sesterterpenoids synthesis of 17-oxo-20-norscalaran-12α,19-<i>o</i>-lactone
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/22c9071ad0a54a288f90c455743d6243
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An Alternative Approach towards C-12 Functionalized Scalaranic Sesterterpenoids Synthesis of 17-Oxo-20-norscalaran-12α,19-<i>O</i>-lactone

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