https://orcid.org/0000-0002-9363-1615
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Abstract
The paper presents the synthesis of some natural diterpenoids of ent-kauranic structure, starting from ent-kaur-16-en-19-oic acid, a natural diterpenoid readily available from the dried wastes of sunflower (Helianthus annuus L.). The reported ent-16α,17-dihydroxykauran-19-oic, ent-16α-hydroxy-17-acetoxykauran-19-oic and ent-16α,17-diacetoxykauran-19-oic acids have been previously isolated from different plant sources and showed diverse biological activities, including anti-HIV, anti-cancer and anti-Alzheimer properties. Their chemical synthesis has not been disclosed so far. Additional cytotoxicity studies of the obtained compounds revealed a remarkable cell proliferative effect of parent ent-kaur-16-en-19-oic acid and two of its synthetic derivatives, which is in line with recent pioneering studies in this area.
Graphical Abstract
Keywords:
- Allylic isomerization
- bioactivity
- cell proliferation
- dihydroxilation
- epoxidation
- ent-kaurane
- ent-16α-hydroxy-17-acetoxykauran-19-oic acid
- ent-kaur-16-en-19-oic acid
- ent-16α17-dihydroxylkauran-19-oic acid
- ent-16
- α,17-diacetoxykauran-19-oic acid
- ent-16α17-epoxykauran-19-oic acid
- ent-17-oxo-16R-kauran-19-oic acid
- ent-17-hydroxykaur-15-en-19-oic acid
- natural diterpenoids