169057-29-8Relevant articles and documents
An efficient route to α,β-epoxy ketones of high enantiomerical purity
Pegorier,Petit,Mambu,Larcheveque
, p. 1403 - 1405 (1994)
Acylepoxides were obtained in high enantiomeric purity (ee = 92-99%) by addition of organolithium or Grignard reagents to enantiomerically pure methyl or ethyl 2,3-epoxypropanoates at low temperature (-85°C).
Total syntheses of kurasoins A and B, novel protein farnesyltransferase inhibitors, and absolute structures of kurasoins A and B
Hirose, Tomoyasu,Sunazuka, Toshiaki,Zhi-Ming, Tian,Handa, Masaki,Uchida, Ryuji,Shiomi, Kazuro,Harigaya, Yoshihiro,Omura, Satoshi
, p. 777 - 784 (2007/10/03)
Asymmetric total syntheses of kurasoins A (1) and B (2), recently discovered protein farnesyltransferase (PFTase) inhibitors, have been achieved in seven steps from 2-(4-hydroxyphenyl)ethanol via the stereospecific alkylation of the chiral epoxide ((-)-7) and in four steps from phenylacetaldehyde via the coupling reaction of the chiral epoxide ((-)- 13) with indole, respectively. The synthesis defined the (3S) absolute configuration of 1 and 2. The stereochemistry of the hydroxy group is important for eliciting PFTase inhibition.