Synthesis of Alstonerine

Structure of Alstonerine

C21H24N2O2

Principal investigator	Stephen F. Martin
Publication year	2007
Synthesis type	Total
Number of steps	15 (linear)
References	Org. Lett. 2007, 9, 1113. J. Org. Chem. 2003, 68, 8867.

Part 1 of 1

intermediate structure

Ac2O, HCl

H2O, HCO2H

RT to 55 °C, 16 h, 63%

See the Bischler-Napieralski Reaction

intermediate structure

Et3N, ClCO2Bn

CH2Cl2, MeOH

-20 °C to RT, 105 min, 76%

intermediate structure

BF3.OEt2, AllylTMS

CH2Cl2

0 °C, 60 min, 72%

See the Hosomi-Sakurai Reaction

intermediate structure

Special reagent

i-Bu2AlH, NaOMe

PhMe, THF

-78 °C to RT, 105 min, 55%

See the Seyferth-Gilbert Homologation

intermediate structure

DMSO, Co2(CO)8

THF

65 °C, 94%

See the Pauson-Khand Reaction

intermediate structure

Boc2O, DMAP

MeCN

99%

intermediate structure

Special reagent

i-Pr3SiH

PhMe

80 °C, 93%

intermediate structure

NaIO4, OsO4

Acetone, H2O

See the Lemieux-Johnson Oxidation

intermediate structure

NaBH4, TsOH

MeOH

55% (2 steps)

intermediate structure

i-Bu2AlH

PhMe

-78 °C

intermediate structure

Et3N, MsCl

CH2Cl2

61% (2 steps)

intermediate structure

Cl3CCOCl

Pyr

65 °C

intermediate structure

Zn

AcOH

75% (2 steps)

intermediate structure

TMSI

MeCN

78%

intermediate structure

MeI, NaH

THF

72%

intermediate structure

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