1384112-63-3Relevant academic research and scientific papers
Synthesis and biological activity of both enantiomers of kujigamberol isolated from 85-million-years-old Kuji amber
Ye, Yue Qi,Koshino, Hiroyuki,Hashizume, Daisuke,Minamikawa, Yuki,Kimura, Ken-Ichi,Takahashi, Shunya
, p. 4259 - 4262 (2012/09/22)
The full-structure of a norlabdane terpenoid, kujigamberol (1) was determined by total synthesis. Key features of the total synthesis are (1) installation of isopentyl group through an o-lithiation of benzamide, (2) construction of tetralone by the RCM reaction, and (3) optical resolution of (±)-1 using chromatographical separation of the corresponding camphanates. X-ray crystallographical analysis of p-bromobenzoate obtained from the more polar camphanate that was identical with a natural derivative, revealed natural kujigamberol to have an S-configuration. Both the natural enantiomer and its (R)-antipode showed the same inhibitory activity toward the mutant yeast and HL-60 cells, while simple analogs without alkyl groups at the C-8 and 9 positions of (±)-1 had no such activity.
