15486-23-4Relevant articles and documents
Stereoselective synthesis of (+)-euphococcinine and (-)-adaline
Arbour, Melissa,Roy, Stephanie,Godbout, Cedrickx,Spino, Claude
supporting information; experimental part, p. 3806 - 3814 (2009/09/25)
(Chemical Equation Presented) We describe the syntheses of (+)-euphococcinine and (-)-adaline, two naturally occurring alkaloids containing a quaternary carbon bearing a nitrogen atom. Key features of the syntheses are a 3,3-sigmatropic rearrangement to give an all-carbon quaternary center, a ring-closing alkene metathesis to give an 8-membered ring, and the use of a single enantiomer of p-menthane-3-carboxaldehyde to make two natural alkaloids of opposite configuration.
Synthesis of homochiral β-sulfinyl nitrones and their application for enantioselective synthesis of (+)-euphococcinine
Murahashi, Shun-Ichi,Sun, Jun,Kurosawa, Hiroyuki,Imada, Yasushi
, p. 557 - 561 (2007/10/03)
Homochiral β-sulfinyl nitrones can be prepared from secondary amines in three steps. Enantioselective synthesis of defensive alkaloid (+)- euphococcinine (9) has been accomplished by means of diastereoselective allylation of homochiral β-sulfinyl nitrone