Chemical Conversion of Vibsanin C to Vibsanin E and Structure of 3-Hydroxyvibsanin E from Viburnum awabuki
- 5 December 1998
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 62 (2) , 337-339
- https://doi.org/10.1021/np980338v
Abstract
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 °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 Viburnum awabuki, has been established by extensive analyses of 2D NMR data and comparison of its spectral data with those of 4.Keywords
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