148906-20-1Relevant articles and documents
Stereoselective intramolecular cyclization of isopentenyl benzamide via π-allylpalladium complex catalyzed by Pd(0)
Joo, Jae-Eun,Mu, Yu,Lee, Yiu-Suk,Tian, Yong-Shou,Lee, Gyu-Jin,Ham, Won-Hun
experimental part, p. 293 - 304 (2010/08/20)
An efficient procedure was developed to synthesize oxazoline as key intermediate in the total synthesis of (+)-lactacystin using palladium(0)-catalyzed intramolecular cyclization of isopentenyl benzamide via a π-allylpalladium complex. A convenient and ef
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.
Cytotoxic agents and methods of use
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Page/Page column 22, (2010/02/14)
Disclosed are compounds that inhibit proteasomic activity in cells. Also disclosed are pharmaceutical compositions comprising such compounds as well as methods to treat conditions, particularly cell proliferative conditions, such as cancer and inflammator
A short, stereocontrolled, and practical synthesis of α-methylomuralide, a potent inhibitor of proteasome function
Saravanan,Corey
, p. 2760 - 2764 (2007/10/03)
An efficient and practical synthesis of α-methylomuralide (3), a selective inhibitor of proteasomes, has been developed as outlined in Scheme 1. Among the advantages of this route of synthesis over previously described approaches are (1) ease of scale-up
A novel and efficient synthesis of a highly active analogue of clasto-lactacystin β-lactone
Soucy, Francois,Grenier, Louis,Behnke, Mark L.,Destree, Antonia T.,McCormack, Teresa A.,Adams, Julian,Plamondon, Louis
, p. 9967 - 9976 (2007/10/03)
Herein, we describe a new convergent synthesis of a more potent analogue of clasto-lactacystin β-lactone (2), PS-519 compound 4, which is currently in preclinical development for the treatment of ischemia-reperfusion injury in stroke and myocardial infarction. The synthetic strategy relies on building two intermediates (an oxazoline and an aldehyde) which are joined through a doubly diastereoselective aldol reaction, setting up the requisite unichiral centers in the final product (4). The facial selectivity and ultimate stereocontrol are achieved by employing a trivalent aluminum Lewis acid, Me2AlCl, in a chelation-induced reaction which yields a single aldol adduct. The efficiency of the synthetic approach has allowed for the preparation of multigram quantities of clinical grade material, which will support Phase I studies.
Total synthesis of (+)-lactacystin
Panek, James S.,Masse, Craig E.
, p. 1093 - 1095 (2007/10/03)
A double stereodifferentiating crotylation between aldehyde 1 and silane (S)-2 to afford homoallylic alcohol 3 is the key diastereoselective step (anti:syn > 30:1) in an efficient asymmetric synthesis of (+)-lactacystin. This compound is a metabolite isol
Total synthesis of (+)-lactacystin
Nagamitsu, Tohru,Sunazuka, Toshiaki,Tanaka, Haruo,Omura, Satoshi,Sprengeler, Paul A.,Smith III, Amos B.
, p. 3584 - 3590 (2007/10/03)
A total synthesis of the novel neurotrophic agent (+)-lactacystin (1) has been achieved in 11 steps and 14% overall yield from (2R,3S)-3-hydroxyleucine [(+)-16]. The construction and bioassay of several active analogs are also described. A new asymmetric approach furnished the four stereoisomers of 3-hydroxyleucine, as required starting materials in high overall yield and enantiomeric purity.
An enantioselective synthesis of (6R)-lactacystin
Corey,Choi, Soongyu
, p. 6969 - 6972 (2007/10/02)
The first enantiospecific, stereocontrolled total synthesis of (6R)-lactacystin, a potential neurotrophic agent, is described.
