e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521
Total synthesis and determination of the absolute configuration of frondosin B
M Inoue, MW Carson, AJ Frontier…
Index: Masayuki, Inoue; Carson, Mattew W.; Frontier, Alison J.; Danishefsky, Samuel J. Journal of the American Chemical Society, 2001 , vol. 123, # 9 p. 1878 - 1889
Two concise syntheses of (±)-frondosin B (1), an interleukin-8 receptor antagonist, have been achieved from commercially available 5-methoxysalicylaldehyde. The seven- membered ring in ketone 33, the common intermediate for both syntheses, was built by a classical Friedel-Crafts reaction. The key step of the first route was facile cationic cyclization of the vinylogous benzofuran to the trisubstituted olefin (30→ 16+ 38) to construct a six- ...
