Expanding Diterpene Complexity and Diversity via Photoinduced Ring Distortions

MARÍA LUZ TIBALDI; VIVIANA NICOTRA; GABRIELA OKSDATH MANSILLA*; MANUELA E. GARCÍA

ChemPlusChem

John Wiley and Sons Inc

Año: 2023

atural products and their semi-synthetic derivatives undoubtedlyconstitute an important source of therapeutic agents. Theirimportance lies in their own origin and evolution, since theyhave great chemical diversity, biochemical specificity, andpharmacological properties. Currently, there is a renewedinterest in the development of methodologies capable ofefficiently modifying the chemical structure of these bioactiveplatforms. In this work, the photoderivatization of the diterpenesolidagenone was performed using a complexity-to-diversityorientedapproach. By exploring [2+2]-photocycloaddition,photoinduced-hydrogen abstraction, and photoxygenation reactions,a set of solidagenone derivatives was obtained,showing different ring fusions, side chain rearrangements, andmodifications of the original furan ring’s substitution pattern.The derivatives obtained were characterised by NMR methodologies.To evaluate the structural diversity of the labdanederivedcompounds, their physicochemical properti