Synthesis of Magallanesine

C21H17NO6

Principal investigator	Takushi Kurihara
Publication year	1994
Synthesis type	Partial
Number of steps	13 (linear)
References	Tetrahedron Lett. 1994, 35, 3749. Tetrahedron 1996, 52, 14563.

Part 1 of 1

H2, Pd/C

4 atm

AcOH, MeOH

RT, 3 h, 99%

"The starting material is obtained in 5 steps from piperonal, see: Chem. Pharm. Bull. 1987, 35, 479."

LiAlH4

THF

RT, 10 min, 93%

SOCl2

CH2Cl2

Reflux, 2 h, 100%

NaOMe

MeOH

Reflux, 90 min, 72%

H2O2

CHCl3, H2O, MeOH

RT, 15 h

THF

Reflux, 60 min, 64% (2 steps)

Pd/C, H2

1 atm

MeOH

RT, 15 h, 100%

NaOH

DME, H2O

RT, 10 min, 94%

Dess-Martin Periodinane

CH2Cl2

RT, 30 min, 95%

See the Dess-Martin Oxidation

HMPA, THF

-78 °C to RT, 90 min

NaHCO3, mCPBA

CH2Cl2

RT, 10 min

PhMe

Reflux, 60 min, 67% (3 steps)

Ph3P, Pd(OAc)2, TlOAc

DMF

130 °C, 24 h, 93%

See the Mizoroki-Heck Reaction