RT journal article
T1 A Biomimetic Approach to Premyrsinane-Type Diterpenoids: Exploring Microbial Transformation to Enhance Their Chemical Diversity
A1 Escobar Montaño, Felipe
A1 Macías Sánchez, Antonio José
A1 Botubol Ares, José Manuel
A1 Durán Patrón, Rosa María
A1 Hernández Galán, Rosario
A2 Química Orgánica
K1 Euphorbia boetica
K1 6,17-epoxylathyrane
K1 epoxyboetirane A
K1 premyrsinane
K1 titanocene
K1 transannular cyclization
K1 Mucor circinelloides
K1 biotransformation
AB 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.
PB MDPI
SN 2223-7747
YR 2024
FD 2024
LK http://hdl.handle.net/10498/33226
UL http://hdl.handle.net/10498/33226
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 06-nov-2026