288404-79-5Relevant academic research and scientific papers
Efficient and diversity-oriented total synthesis of Riccardin C and application to develop novel macrolactam derivatives
Iwashita, Masazumi,Fujii, Shinya,Ito, Shigeru,Hirano, Tomoya,Kagechika, Hiroyuki
, p. 6073 - 6082 (2011/08/22)
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.
Total synthesis of plagiochin D by an intramolecular SNAr reaction
Cortes Morales, Julio Cesar,Guillen Torres, Alejandro,Gonzalez-Zamora, Eduardo
, p. 3165 - 3170 (2011/06/28)
The total synthesis of plagiochin D, a macrocyclic bis(bibenzyl) compound isolated from the liverwort plagiochila acanthophylla, has been accomplished. Closure of the key 16-membered ring, which contained biphenyl ether and biaryl units, was achieved in good yield by an intramolecular SNAr reaction. The Suzuki and Wittig protocols proved to be powerful tools for the construction of a linear precursor that was crucial for ring cyclization. Copyright
