Chemical conversion of vibsanin C to vibsanin E and structure of 3-hydroxyvibsanin E from viburnum awabuki

Vibsanin E (4), a tricyclic vibsane-type diterpene, has been prepared in 50% yield from vibsanin C (2), a seven-membered ring vibsane-type diterpene by reaction with BF3.OEt2 at -78 degrees C. This chemical correlation not only established structure, including absolute configurations, but also has demonstrated a possible biosynthetic route to 4 via 2 derived from vibsanin B (1). The structure of 3-hydroxyvibsanin E (5), another example of a tricyclic seven-membered ring vibsane, isolated from the leaves of Viburnumawabuki, has been established by extensive analyses of 2D NMR data and comparison of its spectral data with those of 4.