Synthesis of Coccinelline

Structure of Coccinelline

C13H23NO

Principal investigatorRobert V. Stevens
Publication year1979
Synthesis typeTotal
Number of steps 11 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
NaOMe
MeOH
RT, 12 h, 58%
intermediate structure
HC(OMe)3, TsOH
MeOH
RT, 12 h, 98%
intermediate structure
NaCl
DMF, H2O
Reflux, 35 h, 69%
intermediate structure
NaH
DME
Reflux, 17 h
intermediate structure
NaCl
DMF, H2O
Reflux, 35 h, 67% (2 steps)
intermediate structure
NaBH3CN, NH4OAc
MeOH
RT, 24 h, 99%
intermediate structure + intermediate structure
HCl, NaOH
H2O, Buffer (pH = 5.5)
RT, 2 d, 75%
intermediate structure
NaCl
DMF, H2O
Reflux, 4 h, 56%
intermediate structure
n-BuLi, Ph3P+CH3 Br-
Et2O
RT to Reflux, 90 min, 82%
See the Wittig Reaction
intermediate structure
H2, Pd/C
MeOH
RT, 8 h
intermediate structure
mCPBA
CH2Cl2
0 °C, 8 h, 64% (2 steps)
intermediate structure