Synthesis of Aspidophytine

C22H26N2O4
Principal investigator | Elias J. Corey |
---|---|
Publication year | 1999 |
Synthesis type | Total |
Number of steps | 20 (3 parts) |
References |
Part 1 of 3


KOH,
MeI,
n-Bu4N+ I-
THF
RT, 3 h, 94%



LiAlH4
THF
0 °C to Reflux, 60 min, 88%

Part 2 of 3
+




Na(Hg)
MeOH
RT, 2 h, 82%

DMAP,
Ac2O
CH2Cl2, Et3N
RT, 60 min, 97%


EDC,
DMAP
i-PrOH
40 °C, 3 h, 57% (2 steps)


NaIO4
H2O, THF
RT, 35 min, 98%

Part 3 of 3
+



NaOH
EtOH
75 °C, 20 h, 88%

K3Fe(CN)6,
NaHCO3
H2O, t-BuOH
RT, 5 min, 92%

OsO4,
DMAP
H2O, t-BuOH


- TMS2NK
- PhNTf2
THF
-78 °C, 30 min, 54%

