77486-53-4Relevant academic research and scientific papers
Total Synthesis of Sophorapterocarpan A, Maackiain, and Anhydropisatin: Application of a 1,3-Michael-Claisen Annulation to Aromatic Synthesis
Ozaki, Yutaka,Mochida, Keiko,Kim, Sang-Won
, p. 1219 - 1224 (2007/10/02)
A new synthetic route to the pterocarpans using a annulation is described. 1,3-Michael-Claisen condensation of α-methylene-γ-butyrolactones with α-sulphur-substituted ketones gives 6-membered rings which have been converted into the pterocarpan framework by aromatization.Sophorapterocarpan A, maackiain, and anhydropisatin have been prepared employing this new aromatic synthesis.
Rearrangements of 2-Phenylthioethanols with Alkenyl, Alkynyl, Ester, and Other Functionalised Alkyl Substituents at the Migration Origin: Synthesis of γ-Phenylthiocrotonate Esters
Brownbridge, Peter,Hunt, Paul G.,Warren, Stuart
, p. 1695 - 1706 (2007/10/02)
The effects of functional groups near the migration origin in and PhS shifts are explored: an α-CO2R group prevents migration, α or β vinyl groups have only steric effects, alkynyl or CO2Et groups encourage rearrangement and provide routes to γ-phenylthio unsaturated esters and ketones.
REGIOSPECIFIC ALLYLATION OF SULFUR SUBSTITUTED ACTIVE METHYLENE COMPOUNDS WITH ALLYLIC BROMIDES
Ono, Noboru,Miyake, Hideyoshi,Tanabe, Yo,Tanaka, Kazuhiko,Kaji, Aritsune
, p. 1365 - 1368 (2007/10/02)
Allylation of sulfur substituted active methylene compounds such as RSCH2Y with allylic bromides in the presence of bases gives a mixture of the SN2-product and the apparent SN2'-product.The former product is selectively obtained in alkylation in a nonpolar solvent.Synthetic utility of this regiospecific allylation is demonstrated in the simple synthesis of pellitorine.
