64190-49-4Relevant articles and documents
Chemical synthesis enables biochemical and antibacterial evaluation of streptolydigin antibiotics
Pronin, Sergey V.,Martinez, Anthony,Kuznedelov, Konstantin,Severinov, Konstantin,Shuman, Howard A.,Kozmin, Sergey A.
, p. 12172 - 12184 (2011/10/04)
Inhibition of bacterial transcription represents an effective and clinically validated anti-infective chemotherapeutic strategy. We describe the evolution of our approach to the streptolydigin class of antibiotics that target bacterial RNA polymerases (RN
SN2 ring opening of β-lactones: An alternative to catalytic asymmetric conjugate additions
Nelson, Scott G.,Wan, Zhonghui,Stan, Magdalena A.
, p. 4680 - 4683 (2007/10/03)
Merging catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions with ensuing Grignard-mediated ring opening of the derived enantiomerically enriched β-lactones is presented as a generally useful asymmetric synthesis of β-disubstituted
Synthesis of Optically Active Bifunctional Isoprenoid Building Blocks by Rhodium(I)-Catalyzed Asymmetric Allylamine to Enamine Isomerization
Schmid, Rudolf,Hansen, Hans-Juergen
, p. 1258 - 1275 (2007/10/02)
The application of the known asymmetric allylamine to enamine isomerization methodology to bifunctional C5-isoprenoid allylic amines of types IId and IIe (Scheme 1) is described.It is shown that a number of such substrates can be isomerized with enantioselectivities of >90percent ee using cationic RhI complexes containing (6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine) (BIPHEMP; 9) as asymmetry-inducing ligand (Scheme 2, Tables 1 and 2).Synthetically most useful is the isomerization of the benzyloxy derivative 10a into the (E)-enamine 11a.This isomerization proceeds with very high enantioselectivity (98-99percent ee) and affords, after enamine hydrolysis, the optically active 4-(benzyloxy)-3-methylbutanals ((R)- or (S)-12) in chemical yields of ca. 90percent.In conjunction, a short synthetic route to the starting material 10a has been developed which has a Pd-catalyzed amination of isoprene epoxide (30) as the key step.Thus, convenient and practical access to the optically active aldehydes (R)- and (S)-12 is now at hand.These aldehydes are useful optically active bifunctional building blocks for isoprenoid homologation.