1072145-53-9Relevant articles and documents
Formal synthesis of soybean phytoalexin glyceollin i
Kohno, Yuta,Koso, Masatsugu,Kuse, Masaki,Takikawa, Hirosato
, p. 1826 - 1828 (2014/03/21)
Glyceollins are well-known phytoalexins isolated from soybean (Glycine max). An efficient three-step synthesis was developed for the preparation of the key intermediate in Khupse's glyceollin I synthesis. Claisen rearrangement-cyclization cascade reaction
Multigram synthesis of glyceollin i
Luniwal, Amarjit,Malik, Neha,Erhardt, Paul,Khupse, Rahul,Reese, Michael,Liu, Jidong,El-Dakdouki, Mohammad,Fang, Lei
, p. 1149 - 1162 (2012/01/05)
Scaled-up procedures and preparation of glyceollin I in multigram quantities are described. The synthesis features construction of a cis-fused ring system in high enantiomeric excess after Sharpless asymmetric dihydroxylation of a key intermediate that is initially produced by an intramolecular Wittig reaction to afford the requisite alkene while simultaneously forming the first ring. The overall yield is 12% after 11 steps.
Total syntheses of racemic, natural (-) and unnatural (+) glyceollin I
Khupse, Rahul S.,Erhardt, Paul W.
supporting information; experimental part, p. 5007 - 5010 (2009/05/31)
(Chemical Equation Presented) The first total syntheses of racemic glyceollin I and its enantiomers are described. A Wittig approach was utilized as an entry to the appropriately substituted isoflav-3-ene so that an osmium tetroxide mediated asymmetric dihydroxylation could be deployed for stereospecific Introduction of the 6a-hydroxy group. While using triphenylphosphine hydrobromide, a novel method was found for gently removing MOM from protected phenolic hydroxyl groups present within sensitive systems.