62711-77-7Relevant academic research and scientific papers
Natural product-derived building blocks for combinatorial synthesis. Part 1. Fragmentation of natural products from myxobacteria
Niggemann, Jutta,Michaelis, Katrin,Frank, Ronald,Zander, Norbert,Hoefle, Gerhard
, p. 2490 - 2503 (2007/10/03)
Novel and unique chiral building blocks of high structural diversity were obtained by selective chemical fragmentation of natural products from myxobacteria. Subsequent modification reactions provided primary alcohol and carboxylic acid derivatives, which are suitable for the construction of combinatorial chemical libraries. The single SPOT synthesis of a hybrid structure on a polypropylene membrane was employed to demonstrate the chemical recombination of such rare building blocks on a micro-scale.
Total synthesis of natural (+)-ambruticin
Kende, Andrew S.,Mendoza, Jose S.,Fujii, Yasuhiro
, p. 8015 - 8038 (2007/10/02)
The structurally unique antifungal antibiotic ambruticin (1) has been prepared for the first time in a convergent synthesis. The strategy for its synthesis involved the independent preparation of the enantiomerically pure fragments 19, 31 and 49. The required C(7) - C(8) β-C-glycoside bond was formed by coupling the glycosyl fluoride 19 with the in situ formed vinyl alane derivative 32. Formation of the C(13) - C(14) trans double bond was accomplished by condensation of the sulfone fragment 49 with the aldehyde intermediate 35 leading to the complete skeletal framework of ambruticin. Saponification of 51 and then cleavage of the benzyl protecting groups gave natural ambruticin.
