87421-21-4Relevant articles and documents
Diastereo- And enantioselective synthesis of β-Hydroxy-α-amino acids: Application to the synthesis of a key intermediate for lactacystin
Li, Qiong,Yang, Shao-Bo,Zhang, Zhihui,Li, Lei,Xu, Peng-Fei
supporting information; experimental part, p. 1627 - 1631 (2009/09/24)
The development of a highly efficient and stereoselective methodology for the preparation of β-hydroxy-α- amino acids is described. Nucleophilic addition of enolates of tricyclic iminolactones 1a and 1b to aldehydes in the presence of 6 equiv of lithium chloride in THF at -78 °C leads to aldol adducts in good yield (63-86%) and high diastereoselectivity (up to >25:1 dr). Subsequently, hydrolysis of the aldol adducts under acidic conditions leads to the corresponding β-hydroxy-a-amino acids in good yields (up to 83%) and excellent enantiomeric excesses (99% ee) with good recovery yields of the chiral auxiliaries 6 and 7. This methodology was applied to the facile synthesis of the key intermediate for lactacystin along with several isomers.
An asymmetric total synthesis of sanjoinine G1
Laib, Taoues,Zhu, Jieping
, p. 83 - 86 (2007/10/03)
A convergent total synthesis of sanjoinine G1, a 14-membered cyclopeptide alkaloid was described. Formation of aryl-alkyl ether bond with concomitant construction of macrocycle by way of an intramolecular SNAr reaction was the key step in this synthesis.
Structure of Amino Acids Isolated from Hydrolyzed HV-Toxin M, a Host-soecific Toxin-related Compound Produced by Helminthosporium victoriae
Kono, Yoshiki,Kinoshita, Takeshi,Takeuchi, Setsuo,Daly, J. M.
, p. 505 - 512 (2007/10/02)
The chemistry of several of the specific toxins isolated from a culture medium of the phytopathogenic fungus Helminthosporium victoriae, a causal agent of Victoria blight disease of oat, was studied.The structures of the amino acid components of the isolated HV-toxin M were identified, and the absolute configurations of the asymmetric α-carbons were elucidated as (S) (I - V, Fig. 1), (S) for C-3 of 3-OH-leucine (II), (R) for C-3 of 3-OH-lysine (V) and (Z) for 3-chlorodehydroalanine (VII).The structure of the other toxin simultaneously isolated, HV-toxin H, was found to be identical with victorin C.
