Synthesis of Isodityrosine

Structure of Isodityrosine

C18H20N2O6

Principal investigatorMichael E. Jung
Publication year1999
Synthesis typeTotal
Number of steps 14 (3 parts)
References
Part 1 of 3
intermediate structure
Et3N, Boc2O
Dioxane , H2O
0 °C to RT, 18.5 h, 92%
intermediate structure
CHCl3, NaOH
H2O
Reflux, 4 h, 33% (49% BRSM)
intermediate structure
K2CO3, BnBr
CHCl3, MeOH
Reflux, 4 h, 71%
intermediate structure
(PhSe)2, H2O2
CH2Cl2, H2O
RT, 18 h
See the Dakin Oxidation
intermediate structure
NH3
MeOH
RT, 80 min, 78% (2 steps)
intermediate structure
BnBr, NaHCO3
DMF
RT, 18 h, 76%
intermediate structure
Part 2 of 3
intermediate structure
SOCl2
MeOH
-10 °C to Reflux, 3 h
intermediate structure
Et3N, Boc2O
Dioxane , H2O
0 °C to RT, 18 h, 91% (2 steps)
intermediate structure
KOAc, (dppf)PdCl2, B2Pin2
DMSO
80 °C, 20 h, 81%
intermediate structure
HN(CH2CH2OH)2
EtOH, i-PrOH
RT, 72 h, 58%
intermediate structure
HCl
H2O, THF
RT, 30 min, 89%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
Pyr, Cu(OAc)2
4 A MS
CH2Cl2
RT, 18 h, 60%
intermediate structure
H2, Pd/C
1 atm
THF
RT, 18 h
intermediate structure
HCl
H2O
65 °C, 6 h, 92% (2 steps)
intermediate structure