Synthesis of Preussin

Structure of Preussin

C21H35NO

Principal investigatorWon-Hun Ham
Publication year2000
Synthesis typeTotal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 2 h
intermediate structure
VinylMgBr
THF
0 °C, , 70% (2 steps)
intermediate structure
Ac2O, Pyr
CH2Cl2
RT, , 99%
intermediate structure
Pd(PPh3)4, K2CO3
MeCN
Reflux, , 83%
intermediate structure
  1. 9-BBN
  2. H2O2
  3. H2O
THF
82%
intermediate structure
RuCl3, NaIO4, NaHCO3
CCl4, MeCN, H2O
intermediate structure
NHMeOMe.HCl, DCC, DMAP
CH2Cl2, Et3N
0 °C to RT, 12 h, 80% (2 steps)
intermediate structure
n-C9H19MgBr
THF
-30 to 0 °C, 60 min, 80%
intermediate structure
H2, Pd(OH)2/C
MeOH, AcOH
RT, 24 h, 50%
intermediate structure
CH2O, NaBH3CN
MeCN, AcOH, H2O
20 °C, 4 h, 78%
intermediate structure