کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5220557 1383391 2011 10 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Efficient and diversity-oriented total synthesis of Riccardin C and application to develop novel macrolactam derivatives
کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Efficient and diversity-oriented total synthesis of Riccardin C and application to develop novel macrolactam derivatives
چکیده انگلیسی

Riccardin C (RC, 1) is a macrocyclic bis(bibenzyl) natural product exhibiting remarkable biological activity as a nuclear liver X receptors (LXRs) ligand and a lipid metabolism mediator. RC is expected to be a lead compound to develop drugs for atherosclerotic diseases, and therefore exploiting diversity-oriented synthesis of RC is a promising approach to drug discovery. In this paper, we report novel total synthesis of RC (7.4% overall yield in 16 steps) by using the intramolecular SNAr reaction as key cyclization reaction. This is the first example of efficient macrocyclization using 3-nitro-4-fluorostilbene as an electrophile. The methodology could be applied to synthesize novel lactam analogs of RC. The diversity-oriented synthesis of RC is versatile method for the synthesis of various types of bis(bibenzyl) natural products and their derivatization.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 67, Issue 33, 19 August 2011, Pages 6073-6082
نویسندگان
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