1506-55-4Relevant articles and documents
Evolution of a short route to strychnine by using the samarium-diiodide-induced cascade cyclization as a key step
Beemelmanns, Christine,Reissig, Hans-Ulrich
, p. 8416 - 8425 (2015)
This comprehensive report accounts the development of a highly diastereoselective samarium diiodide-induced cascade reaction of substituted indolyl ketones. The complexity-generating transformation with SmI2 allows the diastereoselective generation of three stereogenic centers including one quaternary center in one step. The obtained tetra- or pentacyclic dihydroindole derivatives are structural motifs of many monoterpene indole alkaloids, and their subsequent transformations gave way to one of the shortest approaches towards strychnine (14 % overall yield in ten steps, or 10 % overall yield in eight steps). During the course of this report we discuss the influence of substituents on the cyclization step, plausible mechanistic scenarios for the SmI2-induced cascade reaction, diastereoselective reductive amination, and regioselective dehydratization protocols towards the pentacyclic core structure of strychnos alkaloids.
Conformationally constrained analogues of diacylglycerol. 12. Ultrapotent protein kinase C ligands based on a chiral 4,4-disubstituted heptono-1,4- lactone template
Lee,Sharma,Wang,Milne,Lewin,Szallasi,Blumberg,George,Marquez
, p. 36 - 45 (2007/10/03)
Conformationally constrained analogues of diacylglycerol (DAG) built on a 5-[(acyloxy)methyl [-5-(hydroxymethyl)tetrahydro-2-furanone template (1, Chart 1) were shown previously to bind tightly to protein kinase Cα (PK- Cα) in a stereospecific manner. The
Novel Synthesis of (R)-(+)-γ-Butyrolactone-γ-3-propionates by Fermenting Baker's Yeast and Enantiomeric Purity Determination Using NMR Technique
Moriuchi, Fumio,Muroi, Hisae,Aibe, Hiroshi
, p. 1141 - 1144 (2007/10/02)
Optically pure (R)-(+)-γ-butyrolactone-γ-3-propionates 1 were prepared by reducing the precourser, 3-ketoheptane-1,5-dicarboxylic acid monoesters, with fermenting baker's yeast.The optical purity (more than 98percent) was determined by means of HPLC analysis and NMR determination.