AI Article Synopsis
- - Brevifoliol is a natural compound derived from the Taxus baccata plant, and researchers developed multiple derivatives (1-8, 10-20) for further study.
- - Modifications included adding acetyl, Troc, and TES groups at specific carbon positions (C-5 and C-13), and various derivatives were created through esterification with different acids.
- - Analysis, particularly using (13)C NMR, confirmed the structure of these compounds and a specific abeo-taxane configuration, leading to ongoing investigation of their biological activity.
Article Abstract
Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl-(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the (13)C NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied.
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| http://dx.doi.org/10.1021/np0304565 | DOI Listing |
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