A new and short method for the synthesis of 2,4-methanoproline.
2,4-Methanoproline, a supposed non-proteinogenic anti-feedant, was synthesised in 5 steps starting from allyl benzyl ether 3 in 10% overall yield with an intramolecular nucleophilic substitution as the key step for the formation of the bicyclic skeleton.
Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure links 653, B-9000 Gent, Belgium.
Thomas
T
Rammeloo
Christian V
CV
Stevens
D011392:Proline / Q000031:analogs & derivatives / Q000138:chemical synthesis*
C450189:2,4-methanoproline; D011392:Proline