1333225-82-3Relevant academic research and scientific papers
Total synthesis of (+)-herboxidiene/GEX 1A
Gómez-Palomino, Alejandro,Pellicena, Miquel,Kr?mer, Katrina,Romea, Pedro,Urpí, Fèlix,Aullón, Gabriel,Padrón, José M.
, p. 1842 - 1862 (2017/03/09)
A total synthesis of (+)-herboxidiene/GEX 1A has been accomplished from (R)- and (S)-lactate esters in a highly efficient manner. Key steps of the synthesis involve substrate-controlled titanium-mediated aldol reactions from chiral lactate-derived ethyl ketones, an oxa-Michael cyclization, an Ireland-Claisen rearrangement, and a Suzuki coupling. Furthermore, computational studies of the oxa-Michael reaction have unveiled the dramatic influence of intramolecular hydrogen bonds on the stereochemical outcome of such cyclizations, whereas biological analyses have clearly proved the important cytoxicity of (+)-herboxidiene/GEX 1A.
Total synthesis of (+)-Herboxidiene from two chiral lactate-derived ketones
Pellicena, Miquel,Kraemer, Katrina,Romea, Pedro,Urpi, Felix
, p. 5350 - 5353 (2011/12/15)
A substrate-controlled synthesis of (+)-herboxidiene from two lactate-derived chiral ketones is described. Remarkably, most of the carbon backbone was constructed through highly stereoselective titanium-mediated aldol reactions and an Ireland-Claisen rear
