1. A Biomimetic Approach to Premyrsinane-Type Diterpenoids: Exploring Microbial Transformation to Enhance Their Chemical Diversity.
- Author
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Escobar-Montaño, Felipe, Macías-Sánchez, Antonio J., Botubol-Ares, José M., Durán-Patrón, Rosa, and Hernández-Galán, Rosario
- Subjects
BIOMIMETICS ,CHEMICAL amplification ,DITERPENES ,NEURODEGENERATION ,RING formation (Chemistry) ,BIOMIMETIC materials - Abstract
Premyrsinane-type diterpenoids have been considered to originate from the cyclization of a suitable 5,6- or 6,17-epoxylathyrane precursor. Their biological activities have not been sufficiently explored to date, so the development of synthetic or microbial approaches for the preparation of new derivatives would be desirable. Epoxyboetirane A (4) is an 6,17-epoxylathyrane isolated from Euphorbia boetica in a large enough amount to be used in semi-synthesis. Transannular cyclization of 4 mediated by Cp
2 TiIII Cl afforded premyrsinane 5 in good yield as an only diasteroisomer. To enhance the structural diversity of premyrsinanes so their potential use in neurodegenerative disorders could be explored, compound 5 was biotransformed by Mucor circinelloides NRRL3631 to give rise to hydroxylated derivatives at non-activated carbons (6–7), all of which were reported here for the first time. The structures and absolute configurations of all compounds were determined through extensive NMR and HRESIMS spectroscopic studies. [ABSTRACT FROM AUTHOR]- Published
- 2024
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