Synthetic Studies toward the Aphidicolin Family of Diterpenoid Natural Products.

ABSTRACT: Herein, we report an investigation of several synthetic strategies to access the aphidicolin family of natural products. Some unsuccessful approaches include strategies featuring Diels-Alder cycloadditions, Cope rearrangement, divinyl cyclopropane-Cope rearrangement, and C-C cleavage "cut-and-sew" reactions. Separating key bond-forming and bond-breaking steps into a two-step "sew-and-cut" strategy, a penta-carbocycle containing the embedded aphidicolin core was synthesized using an intramolecular [2 + 2]-photocycloaddition reaction─the "sew" step─to obtain a "linear" cycloadduct. Additionally, a constitutional "crossed" isomer of this [2 + 2]-adduct was obtained in a condition-dependent manner, providing insight into factors that can be leveraged to alter [2 + 2]-selectivity for complex su

SUBMITTER: Hayward Cooke J 

PROVIDER: S-EPMC12558746 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature