334518-79-5Relevant academic research and scientific papers
Synthesis of a C(4)-C(9) eleutheside template from D-glucal
By, Kolbot,Kelly, Patrick A,Kurth, Mark J,Olmstead, Marilyn M,Nantz, Michael H
, p. 1183 - 1187 (2007/10/03)
D-Glucal is converted to epoxy allylic alcohol 4 using an eight-step sequence that features a stereoselective methyl Grignard addition to an iodo-hexenulose. Epoxide formation via intramolecular iodide displacement occurs subsequent to an unusual hemiacetal reduction protocol involving LiBH4 in n-octanol. Alcohol 4 and the corresponding aldehyde (Z)-14 are potential C(4)-C(9) templates for eleutheside syntheses.
