Preussin

C₂₁H₃₅NO

Part 1 of 1

AllylSnBu₃, Ti(Oi-Pr)₄, (S)-BINOL

CH₂Cl₂
-78 to -20 °C, 36 h, 82 %

Selectivity : 96:02 er
See the Keck Asymmetric Allylation

Ac₂O, I₂

RT, 10 min, 92 %

OsO₄, NaIO₄, 2,6-Lutidine

Dioxane, H₂O
RT, 30 min, 86 %

See the Lemieux-Johnson Oxidation

(S)-BINOL, La(Ot-Bu)₃

THF
-50 °C, 60 h, 73 %

Selectivity : 95:05 dr
See the Henry Reaction

H₂, Pd/C
1 atm

MeOH
RT, 3 h, 90 %

HCl

H₂O
RT, 2 h, 80 %

Boc₂O, NaHCO₃

EtOAc, H₂O
RT, 3 h, 91 %

MsCl, Et₃N

CH₂Cl₂
0 °C to RT, 6 h, 75 %

LiAlH₄

THF
Reflux, 8 h, 60 %