Synthesis of Alkaloid 251F

Structure of Alkaloid 251F

C16H29NO

Principal investigatorJeffrey Aubé
Publication year2002
Synthesis typeTotal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure
NHMeOMe.HCl, BOP reagent
CH2Cl2, Et3N
RT, 24.5 h, 95%
intermediate structure
VinylMgBr
THF
0 °C, 60 min, 95%
intermediate structure
Grubbs catalyst (1st gen.), C2H4
CH2Cl2
RT, 12 h, 93%
intermediate structure + intermediate structure
CuI, MeLi
THF
0 °C to RT, 45 min, 60%
intermediate structure
Na
EtOH, NH3, THF
-78 °C, 10 min, 54%
See the Birch Reduction
intermediate structure
DEAD, Ph3P, Zn(N3)2.2Pyr
RT, 12 h, 100%
intermediate structure
  1. Me2S
  2. O3
CH2Cl2
-78 °C to RT, 24 h, 70%
intermediate structure
NaBH4
EtOH
0 °C, , 78%
intermediate structure
TfOH
CH2Cl2
0 °C, 6 h, 79%
intermediate structure
LiAlH4
Et2O
0 °C, 20 min, 86%
intermediate structure