960492-27-7Relevant academic research and scientific papers
Enantiopure 2,9-Dideuterodecane – Preparation and Proof of Enantiopurity
Christoffers, Jens,Eru?ar, Gülsera,Fsadni, Miriam H.,Golding, Bernard T.,Mitschke, Nico,Roberts, Amy R.,Sadeghi, Majid M.,Wilkes, Heinz
, p. 3854 - 3863 (2021)
(R,R)- and (S,S)-(2,9-2H2)-n-Decane were prepared regio- and stereospecifically in 25–26 % yield over five steps from commercially available enantiopure (R)- and (S)-propylene oxide, respectively. The synthetic procedure involved nucleophilic displacement of (R)- and (S)-4-toluenesulfonic acid 1-methyl-4-pentenyl ester with LiAlD4 to furnish the respective (5-2H)-1-hexenes. Subsequent olefin metathesis and reduction of the double bond furnished the title compounds. The optical purity of (R,R)- and (S,S)-(2,9-2H2)-n-decane could not be determined by chromatography or polarimetry. Therefore, (R,R)- and (R,S)-(5-2H)-3-hydroxy-2-hexanone were prepared from their respective hexenes by Wacker oxidation, followed by enantioselective α-hydroxylation. The enantiopurity could then be determined by NMR spectroscopy because the stereospecifically deuterated hydroxyketones showed separated signals for the subterminal carbon atom (C-5) in the 13C NMR spectrum.
A convergent synthesis of the [4.4]-spiroacetal-γ-lactones cephalosporolides e and F
Brimble, Margaret A.,Finch, Orla C.,Heapy, Amanda M.,Fraser, John D.,Furkert, Daniel P.,O'Connor, Patrick D.
supporting information; experimental part, p. 995 - 1001 (2011/03/19)
A short convergent synthesis of the fungal metabolites cephalosporolides E and F is reported. The key step makes use of a chelation-controlled Mukaiyama aldol reaction to access the key acyclic spiroacetal precursor with the required syn stereochemistry.
Stereoselective synthesis of the bacterial DNA primase inhibitor?Sch 642305 and its C-4 epimer
García-Fortanet, Jorge,Carda, Miguel,Alberto Marco
, p. 12131 - 12137 (2008/02/11)
A convergent stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its non-natural epimer at C-4 is described. A key aspect was the construction of a trans-2,3-disubstituted cyclohexanone system by means of a stereoselective Mich
