Synthesis of Corynantheidol

C19H26N2O
Principal investigator | Albert I. Meyers |
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Publication year | 1991 |
Synthesis type | Total |
Number of steps | 13 (linear) |
References |
Part 1 of 1
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Camphorsulfonic acid
PhMe
Reflux, 2 d, 75%

- (CH2NMe2)2 , KH
- MeOCH2Cl
THF
0 °C, 2.5 h, 99%

- KH , MeLi
- ClCH2CN
THF
-100 to -72 °C, 100 min

NH2NH2.H2O
AcOH, EtOH, H2O
0 °C, ON, 64% (2 steps)


DMAP,
Et3N
CH2Cl2
0 °C, 35 min, 89%


K2CO3
H2O, THF
RT, 60 min, 88% (2 steps)

LiAlH4
THF
Reflux, 4 h, 73%



H2,
K2CO3,
Pd/C
1 atm
EtOAc
RT, ON, 96%

LiAlH4
THF
RT, 60 min, 81%

HCl
Et2O, H2O, THF
RT, 5 h, 80%
