90741-49-4Relevant academic research and scientific papers
Synthetic and Stereochemical Studies Directed Towards Anatoxin-a
Huby, Nicholas J. S.,Kinsman, Richard G.,Lathbury, David,Vernon, Peter G.,Gallagher, Timothy
, p. 145 - 155 (2007/10/02)
The synthesis and stereocontrolled Ag1-catalysed cyclisation of a series of allenic amino esters 8a-e is described.For compounds 8a-d the cis-2,5-disubstituted pyrrolidine 9 is formed exclusively but the primary amine 8e undergoes cyclisation n
Enantiodivergent Synthesis of (+)- and (-)-Anatoxin from L-Glutamic acid
Sardina, F. Javier,Howard, Michael H.,Morningstar, Marshall,Rapoport, Henry
, p. 5025 - 5033 (2007/10/02)
The optically pure 2,5-difunctionalized homotropane 11, prepared from L-glutamic acid, serves as the common, advanced intermediate for the synthesis of either natural (+)-anatoxin (30, 18percent overall yield) or unnatural (-)-anatoxin (33, 30percent overall yield) by selective manipulation of either the C-2 ester or C-5 acetyl functionalities.Side-chain substitution in the decarbonylative iminium ion cyclization of a substituted proline enhanced the yield by 25percent as compared to the unsubstituted parent system.The additional substitution at C-5 of the 9-azabicyclononane ring system allows access to analogues of anatoxin not availalble through other syntheses.
