Synthesis of Highly Functionalized Biologically Active Tetracyclic Diterpenoids from ent-Kaur-16-en-19-oic Acid under Modified Prévost-Woodward Reaction Conditions
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MORĂRESCU (CHETRARU), Olga, GRINCO, Marina, KULCIŢKI, Veaceslav, BARBA, Alic, GARBUZ, Olga, GULYA, Aurelian, UNGUR, Nikon. Synthesis of Highly Functionalized Biologically Active Tetracyclic Diterpenoids from ent-Kaur-16-en-19-oic Acid under Modified Prévost-Woodward Reaction Conditions. In: Russian Journal of Organic Chemistry, 2021, nr. 12(57), pp. 1931-1939. ISSN 1070-4280. DOI: https://doi.org/10.1134/S1070428021120058
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Russian Journal of Organic Chemistry
Numărul 12(57) / 2021 / ISSN 1070-4280

Synthesis of Highly Functionalized Biologically Active Tetracyclic Diterpenoids from ent-Kaur-16-en-19-oic Acid under Modified Prévost-Woodward Reaction Conditions

DOI: https://doi.org/10.1134/S1070428021120058

Pag. 1931-1939

Morărescu (Chetraru) Olga1, Grinco Marina1, Kulciţki Veaceslav1, Barba Alic1, Garbuz Olga2, Gulya Aurelian2, Ungur Nikon1
 
1 Institute of Chemistry,
2 Moldova State University
 
Disponibil în IBN: 2 februarie 2022


Rezumat

A procedure has been developed for the synthesis of highly functionalized tetracyclic diterpenoids from natural ent-kaur-16-en-19-oic acid under modified Prévost–Woodward reaction conditions. The reaction follows an unusual pathway which leads mainly to bromination or rearrangement products. The transforma­tion of ent-kaur-16-en-19-oic acid afforded a mixture of (16ZE)-17-bromo-ent-kaur-16-en-19-oic, (15R,16E)-17-bromo-15-acetoxy-ent-kaur-16-en-19-oic, (16S)-17-bromo-16-acetoxy-ent-kaur-19-oic, (15S)-15-acetoxy-ent-kaur-16-en-19-oic, and (15S)-15-hydroxy-ent-kaur-16-en-19-oic acids, the latter two being reported previously. The newly syn­thesized compounds were evaluated for their cytotoxicity against two cancer cell lines, HeLa and BxPC-3.

Cuvinte-cheie
diterpenoid, ent-kaur-16-en-19-oic acid, Prévost–Woodward reaction