105958-49-4Relevant academic research and scientific papers
Phormidolides B and C, cytotoxic agents from the sea: Enantioselective synthesis of the macrocyclic core
Lorente, Adriana,Gil, Alejandro,Fernndez, Rogelio,Cuevas, Carmen,Albericio, Fernando,lvarez, Mercedes
, p. 150 - 156 (2015)
New cytotoxic polyketide macrolides named phormidolides B and C were isolated from a marine sponge of the Petrosiidae family collected off the coast of Pemba (Tanzania). The isolation, structure elucidation, and enantioselective synthesis of three diastereomers of the macrocyclic core is described herein. The described synthetic methodology started from 2-deoxy-d-ribose or 2-deoxy-l-ribose and afforded the desired macrocycles with high enantiomeric purity. The key step of the synthesis is the formation of the Z-trisubstituted double bond using a Julia-Kocienski olefination. The versatility of the synthetic methodology may provide access to other enantiopure macrocycles by making changes in the starting materials or chiral inductors.
A General Method for determining the Anomeric Configuration of C-Furanoside Derivatives: a 1H Nuclear Magnetic Resonance Nuclear Overhauser Effect Study
Bernstein, Michael A.,Morton, Howard E.,Guindon, Yvan
, p. 1155 - 1164 (2007/10/02)
The nuclear Overhauser effect 1H n.m.r. experiment was found to be an excellent method for a priori determination of the stereochemical configuration of a variety of C-furanoside derivatives.If the stereochemistry at one ring carbon atom is kno
