SOMMAIRE

J.MAR.CHIM.HETEROCYCL. Volume 1, N° 1 Décembre 2002
R
CH 3
N
O
1
OH
O
O
PCl 3
HCl gas
R
CH 2Cl 2, 0°C _N
CH 3
R
CH 3
N
2a : R= H, 2b : R= CH3, 2c : R= i.C3H7, 2d : R= C6H5, 2e : R= CH2Ph
45
2
O
O
O
O
Scheme1
Cl
O
O
R
CH 3
N
O
O
O , Cl
Moreover investigations on the aliyclic β-aminoacids have been recur a considerable attention
[14]. The aliyclic N-carboxy- β-aminoacid anhydrides could considered as starting material for the
preparation of modified (unnatural) analogues of biologically active peptides. By insertion of an
alicyclic β-aminoacid scaffold in place of the α-aminoacid one of a naturally occurring
pharmacologically active peptides, the activity or the effect of these structures could be modified.
By means of such exchanges, stabilities of the natural peptides could be increased because the βpeptides
are resistant to enzymatic degradation [15]. On the other hand, alicyclic N-carboxy- βaminoacid
only can be used as starting material to access different heterocycles, potential
pharmacons, for the synthesis of natural products or analogues and constitutes also a building
bullocks in drug research.
Our approach was extended successfully to N-carboxy-β-aminoacid anhydrides which are not
easily obtained by other methods [16] (Scheme 2).
=
CH 3
NHBoc
CO 2H
PCl 3
CH 2Cl 2
O
3 4
Scheme 2
CH 3
N O
4a CH2 , 4b ,
4c , 4d
H
, 4e
H
CH2 N
H
H
Cis Trans
O