One - step selective synthesis of 13-epi-manoyl oxide
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547.913:543.2 (2)
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MORĂRESCU (CHETRARU), Olga, TRAISTARI, Marionela, BARBA, Alic, DUKA, Gh., UNGUR, Nikon, KULCIŢKI, Veaceslav. One - step selective synthesis of 13-epi-manoyl oxide. In: Chemistry Journal of Moldova, 2021, nr. 1(16), pp. 99-104. ISSN 1857-1727. DOI: https://doi.org/10.19261/cjm.2021.820
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Chemistry Journal of Moldova
Numărul 1(16) / 2021 / ISSN 1857-1727 /ISSNe 2345-1688

One - step selective synthesis of 13-epi-manoyl oxide

DOI: https://doi.org/10.19261/cjm.2021.820
CZU: 547.913:543.2

Pag. 99-104

Morărescu (Chetraru) Olga1, Traistari Marionela2, Barba Alic1, Duka Gh.1, Ungur Nikon1, Kulciţki Veaceslav1
 
1 Institute of Chemistry,
2 Moldova State University
 
Disponibil în IBN: 30 iunie 2021


Rezumat

The selective one-step synthesis of 13-epi-manoyl oxide is reported based on a low-temperature superacidic cyclization of sclareol. The reaction conditions have been finely tuned in order to achieve a 9:1 ratio between epimeric oxides in favour of the desired 13-epi-oxide. The structures were confirmed by 1H and 13C NMR, and composition of the crude reaction products determined by GC-MS. These results have been interpreted by a hypothetical SN2 mechanism which occurs with inversion of configuration around the C-13 chiral center of the starting substrate. The preparative value of the elaborated procedure is demonstrated on a gram-scale experiment.

Cuvinte-cheie
sclareol, cyclization, superacid, ether, labdane