Epibatidine

Author	Alan Armstrong
Publication year	2007
Synthesis type	Total synthesis
Number of steps	10 (linear)
References	J. Org. Chem. 2007, 72, 8019. Org. Lett. 2005, 7, 1335. Chem. Commun. 2004, 812.

Part 1 of 1

TsNClNa, NBS

MeCN
RT, 60 min, 79 %

VinylMgBr

Et₂O
-30 °C to RT, 10 min, 56 %

See the Grignard Reaction

SnCl₄

CH₂Cl₂
0 °C to RT, 14.5 h, 32 %

See the Prins Reaction
See the Pinacol Rearrangement

CrO₃, H₂SO₄

Acetone, H₂O
0 °C to RT, 100 min, 92 %

See the Jones Oxidation

(COCl)₂

CH₂Cl₂
Reflux, 20 min

BrCCl₃
hν

RT to 90 °C, 65 min, 61 % (2 steps)

See the Barton Decarboxylation

PhOH, HBr

H₂O
Reflux, 105 min

Boc₂O, Na₂CO₃

THF, H₂O
RT, 2.5 d, 67 % (2 steps)

Ni(cod)₂, KOt-Bu

s-BuOH
RT to 60 °C, 56 %

See the Suzuki Coupling
The yield was 66 % brsm.

CF₃CO₂H

CH₂Cl₂
RT, 5 h, 89 %