Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
10596585 | Bioorganic & Medicinal Chemistry Letters | 2012 | 4 Pages |
Abstract
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
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Chemistry
Organic Chemistry
Authors
Yue Qi Ye, Hiroyuki Koshino, Daisuke Hashizume, Yuki Minamikawa, Ken-ichi Kimura, Shunya Takahashi,