Synthesis of Corynantheidol

Structure of Corynantheidol

C19H26N2O

Principal investigatorAlbert I. Meyers
Publication year1991
Synthesis typeTotal
Number of steps 13 (linear)
References
J. Org. Chem. 1991, 56, 2091. J. Am. Chem. Soc. 1988, 110, 4778.
Part 1 of 1
intermediate structure + intermediate structure
Camphorsulfonic acid
PhMe
Reflux, 2 d, 75%
intermediate structure
  1. (CH2NMe2)2 , KH
  2. MeOCH2Cl
THF
0 °C, 2.5 h, 99%
intermediate structure
  1. KH , MeLi
  2. 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
DMAP, Et3N
CH2Cl2
0 °C, 35 min, 89%
intermediate structure
Zn-Ag
)))
THF
40 °C, 2 h
See the Blaise Reaction
intermediate structure
K2CO3
H2O, THF
RT, 60 min, 88% (2 steps)
intermediate structure
LiAlH4
THF
Reflux, 4 h, 73%
intermediate structure
DMSO, Et3N, (CF3CO)2O
CH2Cl2
-78 °C to RT, 100 mnin, 85%
See the Swern Oxidation
intermediate structure
NaH, (MeO)2P(O)CH2CO2Me
THF
0 to 50 °C, 4.5 h, 83%
See the Horner-Wadsworth-Emmons Reaction
intermediate structure
H2, K2CO3, Pd/C
1 atm
EtOAc
RT, ON, 96%
intermediate structure
LiAlH4
THF
RT, 60 min, 81%
intermediate structure
HCl
Et2O, H2O, THF
RT, 5 h, 80%
intermediate structure
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