Synthesis of Preussin

Structure of Preussin

C21H35NO

Principal investigatorNabin C. Barua
Publication year2006
Synthesis typeTotal
Number of steps 9 (linear)
References
Part 1 of 1
intermediate structure
AllylSnBu3, (S)-BINOL, Ti(Oi-Pr)4
CH2Cl2
-78 to -20 °C, 36 h, 82%
intermediate structure
Ac2O, I2
RT, 10 min, 92%
intermediate structure
2,6-Lutidine, OsO4, NaIO4
Dioxane , H2O
RT, 30 min, 86%
intermediate structure + intermediate structure
(S)-BINOL, La(Ot-Bu)3
THF
-50 °C, 60 h, 73%
See the Henry Reaction
intermediate structure
H2, Pd/C
MeOH
RT, 3 h, 90%
intermediate structure
HCl
H2O
RT, 2 h, 80%
intermediate structure
NaHCO3, Boc2O
EtOAc, H2O
RT, 3 h, 91%
intermediate structure
Et3N, MsCl
CH2Cl2
0 °C to RT, 6 h, 75%
intermediate structure
LiAlH4
THF
Reflux, 8 h, 60%
intermediate structure