Synthesis and stereochemical analysis of 2-amino-1,2,3,4-tetrahydro-1,4-methanonaphthalene-2-carboxylic acid, a conformationally rigid phenylalanine derivative

Conformationally rigid cyclic α-amino acids in the design of peptidomimetics, peptide models and biologically active compounds

“…Another approach utilises the classical Strecker and Bucherer ± Lieb reactions 204,205,217,218 starting from 2-norbornanone, which in turn is produced by the Diels ± Alder reaction.…”

“…Numerous CRA with the norbornane cage have been prepared. In addition to the unsubstituted acid 144, various functionalised derivatives 146 ± 155 (which represent analogues of phenylalanine, 208,209,217 tyrosine, 217 aspartic acid, 211,212 serine, 213 methionine, 219 glutamic acid 211, 219 ± 221 ), including polyhydroxy-compounds 156a ± d 216 have been prepared. All of these compounds are fully w-rigid (except for 152, which is w 1 -rigid).…”