Synthesis of Triquinacene

Structure of Triquinacene

C10H10

Principal investigatorJames M. Cook
Publication year1989
Synthesis typeTotal
Number of steps 8 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
K2CO3, NaHCO3
H2O, MeOH
RT, 3 d, 45%
intermediate structure
CH2N2
CH2Cl2
RT, 2 h, 90%
intermediate structure
KH, Allyl-I
DMF
-58 to -25 °C, 6 h
intermediate structure
HCl
AcOH, H2O
Reflux, 90 min, 90% (2 steps)
intermediate structure
  1. Me2S
  2. O3
EtOAc
-58 °C, , 81%
intermediate structure
HCl
H2O, THF
RT, 7 d, 86%
See the Aldol Addition
intermediate structure
BH3.THF
THF
0 °C, 16 h, 93%
intermediate structure
HMPA
Reflux, 2 d, 80%
intermediate structure