Synthesis of Magallanesine

Structure of Magallanesine

C21H17NO6

Principal investigatorTakushi Kurihara
Publication year1994
Synthesis typePartial
Number of steps 13 (linear)
References
Part 1 of 1
intermediate structure
H2, Pd/C
AcOH, MeOH
RT, 3 h, 99%
"The starting material is obtained in 5 steps from piperonal, see: Chem. Pharm. Bull. 1987, 35, 479."
intermediate structure
LiAlH4
THF
RT, 10 min, 93%
intermediate structure
SOCl2
CH2Cl2
Reflux, 2 h, 100%
intermediate structure
NaOMe
MeOH
Reflux, 90 min, 72%
intermediate structure
H2O2
CHCl3, H2O, MeOH
RT, 15 h
intermediate structure
THF
Reflux, 60 min, 64% (2 steps)
intermediate structure
H2, Pd/C
MeOH
RT, 15 h, 100%
intermediate structure + intermediate structure
NaOH
DME, H2O
RT, 10 min, 94%
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 30 min, 95%
intermediate structure
  1. TMS2NNa
  2. (PhS)2
HMPA, THF
-78 °C to RT, 90 min
intermediate structure
mCPBA, NaHCO3
CH2Cl2
RT, 10 min
intermediate structure
PhMe
Reflux, 60 min, 67% (3 steps)
intermediate structure
Pd(OAc)2, Ph3P, TlOAc
DMF
130 °C, 24 h, 93%
See the Heck Coupling
intermediate structure