57103-57-8Relevant articles and documents
Multigram synthesis of glyceollin i
Luniwal, Amarjit,Malik, Neha,Erhardt, Paul,Khupse, Rahul,Reese, Michael,Liu, Jidong,El-Dakdouki, Mohammad,Fang, Lei
experimental part, 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.
Biomimetic syntheses and antiproliferative activities of racemic, natural (-), and unnnatural (+) glyceollin i
Khupse, Rahul S.,Sarver, Jeffrey G.,Trendel, Jill A.,Bearss, Nicole R.,Reese, Michael D.,Wiese, Thomas E.,Boue, Stephen M.,Burow, Matthew E.,Cleveland, Thomas E.,Bhatnagar, Deepak,Erhardt, Paul W.
, p. 3506 - 3523 (2011/07/30)
A 14-step biomimetic synthetic route to glyceollin I (1.5% overall yield) was developed and deployed to produce the natural enantiomeric form in soy, its unnatural stereoisomer, and a racemic mixture. Enantiomeric excess was assessed by asymmetric NMR shift reagents and chiral HPLC. Antiproliferative effects were measured in human breast, ovarian, and prostate cancer cell lines, with all three chiral forms exhibiting growth inhibition (GI) in the low to mid μM range for all cells. The natural enantiomer, and in some cases the racemate, gave significantly greater GI than the unnatural stereoisomer for estrogen receptor positive (ER+) versus ER- breast/ovarian cell lines as well as for androgen receptor positive (AR+) versus AR - prostate cancer cells. Surprisingly, differences between ER + and ER- cell lines were not altered by media estrogen conditions. These results suggest the antiproliferative mechanism of glyceollin I stereoisomers may be more complicated than strictly ER interactions.
