کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
10596585 981907 2012 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis and biological activity of both enantiomers of kujigamberol isolated from 85-million-years-old Kuji amber
کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis and biological activity of both enantiomers of kujigamberol isolated from 85-million-years-old Kuji amber
چکیده انگلیسی
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
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 22, Issue 13, 1 July 2012, Pages 4259-4262
نویسندگان
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