Synthesis of Corynantheidol

Structure of Corynantheidol

C19H26N2O

Principal investigatorAlbert I. Meyers
Publication year1991
Synthesis typeTotal
Number of steps 13 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Camphorsulfonic acid
PhMe
Reflux, 2 d, 75%
intermediate structure
  1. KH
  2. (CH2NMe2)2
  3. MeOCH2Cl
THF
0 °C, 2.5 h, 99%
intermediate structure
  1. KH
  2. MeLi
  3. ClCH2CN
THF
-100 to -72 °C, 100 min
intermediate structure
NH2NH2.H2O
AcOH, EtOH, H2O
0 °C, ON, 64% (2 steps)
intermediate structure + intermediate structure
Et3N, DMAP
CH2Cl2
0 °C, 35 min, 89%
intermediate structure
Zn-Ag
THF
40 °C, 2 h
See the Blaise Reaction
intermediate structure
K2CO3
THF, H2O
RT, 60 min, 88% (2 steps)
intermediate structure
LiAlH4
THF
Reflux, 4 h, 73%
intermediate structure
(CF3CO)2O, DMSO, Et3N
CH2Cl2
-78 °C to RT, 100 mnin, 85%
See the Swern Oxidation
intermediate structure
(MeO)2P(O)CH2CO2Me, NaH
THF
0 to 50 °C, 4.5 h, 83%
intermediate structure
H2, Pd/C, K2CO3
EtOAc
RT, ON, 96%
intermediate structure
LiAlH4
THF
RT, 60 min, 81%
intermediate structure
HCl
THF, Et2O, H2O
RT, 5 h, 80%
intermediate structure