708212-82-2Relevant academic research and scientific papers
Characterization of an abeo-taxane: Brevifoliol and derivatives
Tremblay, Steve,Soucy, Chantal,Towers, Neil,Gunning, Philip J.,Breau, Livain
, p. 838 - 845 (2007/10/03)
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 13C 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.
