AI Article Synopsis
- Transannular cyclization of germacrone-4,5-epoxide under basic conditions produced four products, differing from results obtained under acidic and thermal conditions.
- One of the products is an isomer of the starting material, while the other three are new eudesmane-type derivatives.
- The new compounds were characterized using various advanced techniques, and although they share a similar carbon skeleton with eudesmane-type compounds, they have distinct arrangements of isoprene units.
Article Abstract
Transannular cyclizations of germacrone-4,5-epoxide under acidic and thermal conditions have been reported in our previous study. However, this process gave the different and interesting results under basic conditions. (4S,5S)-Germacrone-4,5-epoxide (1) was treated under basic conditions to yield four products (2-5). Compound 2 was an isomer of 1--(4S,5S,9Z)-4,5-epoxygermacra-7(11),9-dien-8-one--and the remaining three compounds (3-5) were eudesmane-type derivatives. Compounds 4 and 5 are new compounds. The structures of the new compounds were determined using high resolution (HR)-MS, one dimensional (1D)-NMR, 2D-NMR and circular dichroism (CD) spectroscopic data. Products 3-5 had the same carbon skeleton as that of eudesmane-type compounds; however, these compounds showed different arrangement of isoprene units to the natural eudesmane-type sesquiterpenes.
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| http://dx.doi.org/10.1248/cpb.c14-00130 | DOI Listing |
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