%0 Journal Article 
%A Escobar Montaño, Felipe
%A Macías Sánchez, Antonio José
%A Botubol Ares, José Manuel
%A Durán Patrón, Rosa María
%A Hernández Galán, Rosario
%T A Biomimetic Approach to Premyrsinane-Type Diterpenoids: Exploring Microbial Transformation to Enhance Their Chemical Diversity
%D 2024
%@ 2223-7747
%U http://hdl.handle.net/10498/33226
%X 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 Cp2TiIIICl 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.
%K Euphorbia boetica
%K 6,17-epoxylathyrane
%K epoxyboetirane A
%K premyrsinane
%K titanocene
%K transannular cyclization
%K Mucor circinelloides
%K biotransformation
%~ Universidad de Cádiz