Synthesis of Murrayazoline

Structure of Murrayazoline

C23H25NO

Principal investigatorNoritaka Chida
Publication year2008
Synthesis typeTotal
Number of steps 22 (3 parts)
References
Part 1 of 3
intermediate structure
Et3N, TsCl
CH2Cl2
0 °C, 4 h
intermediate structure
NIS
DMF
0 °C to RT, 60 min, 76% (2 steps)
intermediate structure + intermediate structure
Na2CO3, Pd(PPh3)4
EtOH, H2O, PhH
Reflux, 3 h, 99%
See the Suzuki Coupling
intermediate structure
  1. CuBr
  2. H2SO4
  3. HBr
  4. NaNO2
AcOH, H2O
0 to 80 °C, 14 h, 92%
intermediate structure
NaOMe
MeOH
Reflux, 8 h
intermediate structure
MeOCH2Cl, NaH
DMF
0 °C to RT, 90 min, 92% (2 steps)
intermediate structure
Part 2 of 3
intermediate structure
TMS2NK, Ph3P+CH2OMe Cl-
PhMe
0 to 120 °C, 4 h
See the Wittig Reaction
intermediate structure
HCl
H2O, THF
RT, 12 h, 74% (2 steps)
intermediate structure
MeLi
Et2O
-78 °C, 60 min, 92%
intermediate structure
NMO, n-Pr4N+ RuO4-
CH2Cl2
RT, 30 min, 85%
intermediate structure
MeLi
Et2O
-78 °C, 2 h, 64%
intermediate structure
BF3.OEt2, TsOH, TMSN3
PhH
0 °C, 30 min
intermediate structure
CuSO4, Me3O+BF4-
CH2Cl2, H2O
0 °C to RT, 14 h, 61% (2 steps)
intermediate structure
Et3N, TMS2NK, TMSCl
THF
-78 °C, 40 min
intermediate structure
Pd(OAc)2
MeCN
RT, 4 h, 84% (2 steps)
intermediate structure
TMSOTf, (TMSOCH2)2
CH2Cl2
-78 to -15 °C, 90 min, 99%
intermediate structure
LiAlH4
THF
0 °C, 2 h, 87%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
Pd2(dba)3, NaOt-Bu
PhMe
130 °C, 13 h, 59%
intermediate structure
Sc(OTf)3
DCE, H2O
120 °C, 36 h, 73%
intermediate structure
DMAP, Et3N, Tf2O
CH2Cl2
0 °C, 60 min, 94%
intermediate structure
MeMgBr
Et2O
0 °C, 60 min, 77%
intermediate structure
Pd(OAc)2
PhMe
120 °C, 20 h, 80%
intermediate structure