Total synthesis of nine longiborneol sesquiterpenoids using a functionalized camphor strategy.

ABSTRACT: Natural product total synthesis inspires the development of synthesis strategies to access important classes of molecules. In the 1960s, Corey and coworkers demonstrated a visionary preparation of the terpenoid longifolene, using 'strategic bond analysis' to craft a synthesis route. This approach proposes that efficient synthesis routes to bridged, polycyclic structures should be formulated to introduce the bulk of the target's topological complexity at a late stage. Subsequently, similar strategies have proved general for the syntheses of a wide variety of bridged, polycyclic molecules. Here, we demonstrate that an orthogonal strategy where topological complexity is introduced at the outset leads to the short synthesis of the longifolene-related terpenoid longiborneol. To implement this s

SUBMITTER: Lusi RF 

PROVIDER: S-EPMC9117171 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature