Xylopiana A, a Dimeric Guaiane with a Case-Shaped Core from Xylopia vielana: Structural Elucidation and Biomimetic Conversion

Xylopiana
A (1), a dimeric guaiane with an unprecedented
pentacyclo­[5.2.1.01,2.04,5′.05,4′]­decane-3,2′-dione core, and three biosynthetically related
intermediates, compounds 2–4, were
isolated from the leaves of Xylopia vielana. Their structures and absolute configurations were determined by
a combination of spectroscopic data, X-ray crystallography, electronic
circular dichroism calculations, and chemical conversion. The structure
of known vielanin A was revised to be compound 3. Compound 4 exerted a 3.7-fold potentiation effect on doxorubicin susceptibility
at the tested concentration of 10 μM.