Synthesis of Alstonerine

Structure of Alstonerine

C21H24N2O2

Principal investigatorStephen F. Martin
Publication year2007
Synthesis typeTotal
Number of steps 15 (linear)
References
Part 1 of 1
intermediate structure
Ac2O, HCl
H2O, HCO2H
RT to 55 °C, 16 h, 63%
intermediate structure
Et3N, ClCO2Bn
CH2Cl2, MeOH
-20 °C to RT, 105 min, 76%
intermediate structure
BF3.OEt2, AllylTMS
CH2Cl2
0 °C, 60 min, 72%
intermediate structure
i-Bu2AlH, NaOMe
PhMe, THF
-78 °C to RT, 105 min, 55%
intermediate structure
DMSO, Co2(CO)8
THF
65 °C, , 94%
intermediate structure
DMAP, Boc2O
MeCN
99%
intermediate structure
i-Pr3SiH
PhMe
80 °C, , 93%
intermediate structure
OsO4, NaIO4
Acetone, H2O
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