121904-08-3Relevant academic research and scientific papers
Stereoselective synthesis of bicyclic tetrahydrofuran-fused β-lactams and their conversion into methyl cis-3-aminotetrahydrofuran-2-carboxylates
Mollet, Karen,D'Hooghe, Matthias,De Kimpe, Norbert
, p. 10787 - 10793 (2013/01/15)
cis-3-Benzyloxy-4-(2-mesyloxyethyl)azetidin-2-ones were shown to be useful starting products for the synthesis of cis-2-oxa-6-azabicyclo[3.2.0]heptan-7- ones in high overall yields and purity upon hydrogenolysis of the benzyl ether substituent followed by
Asymmetric synthesis of (2S,3R)-capreomycidine and the total synthesis of capreomycin IB
DeMong, Duane E.,Williams, Robert M.
, p. 8561 - 8565 (2007/10/03)
A 27 step total synthesis of the tuberculostatic macrocyclic peptide antibiotic capreomycin IB has been accomplished. The synthesis features the use of an enolate-aldimine condensation between a chiral glycine aluminum enolate and the benzyl imine of 3-tert-butyldimethylsiloxy-propanal as a means of preparing the cyclic guanidine amino acid (2S,3R)-capreomycidine. Additionally, a Hofmann rearrangement was exacted on a late-stage pentapeptide in order to transform an asparagine residue into a diaminopropanoic acid residue.
The asymmetric synthesis of (2S,3R)-capreomycidine
DeMong, Duane E.,Williams, Robert M.
, p. 3529 - 3532 (2007/10/03)
An improved asymmetric synthesis of the guanidine-containing amino acid (2S,3R)-capreomycidine has been achieved in seven steps and 28% overall yield. The key synthetic step involved a Mannich-type reaction between a chiral glycine aluminum enolate and the benzyl-imine of 3-tert-butyldimethylsiloxy-propionaldehyde.
