Synthesis of Panaxytriol

Structure of Panaxytriol

C17H26O3

Principal investigatorSamuel J. Danishefsky
Publication year2003
Synthesis typeTotal
Number of steps 9 (3 parts)
References
Part 1 of 3
intermediate structure
CBS Reagent, BH3.Me2S
THF
-30 °C, 10 min, 75%
">99:01 e.r."
intermediate structure
AgNO3, NBS
Acetone
RT, 1 h, 100%
intermediate structure
Part 2 of 3
intermediate structure
Imidazole, TBSCl
DMF
0 °C to RT, 6 h, 99%
intermediate structure
AD-mix B
H2O, t-BuOH
0 °C, 42 h, 100%
">99:01 e.r."
intermediate structure
TsOH, 2,2-Dimethoxypropane
CH2Cl2
RT, 1 h
intermediate structure
Ph3PBr2
CH2Cl2
RT, 30 min, 90% (2 steps)
See the Appel Reaction
intermediate structure
  1. HCl
  2. K2CO3
EtOH, H2O
RT, 3.5 d, 72% (89% BRSM)
intermediate structure
LiCCH.(CH2NH2)2
HMPA, THF
0 °C to RT, ON, 80%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
CuCl, Et2NH, NH2OH.HCl
CH2Cl2, MeOH
0 °C, 2 h, 63%
intermediate structure