Synthesis of Pentacycloanammoxic Acid

C20H30O2
Principal investigator | Elias J. Corey |
---|---|
Publication year | 2004 |
Synthesis type | Total |
Number of steps | 15 (linear) |
References |
Part 1 of 1

Br2


H2,
NaNO2,
PtO2
1 atm
EtOH, THF
RT

Zn
AcOH
95 °C, 60 min, 80% (2 steps)

2-Cyclopentenone
hν
MeCN
RT, 12 h, 40%

- H2 , Pd/C
- O2
1 atm
EtOH
RT, 2.5 h, 76%

HC(OMe)3,
TsOH
MeOH
40 °C, 60 min, 91%

AcOH
hν
H2O, MeCN
50 °C, 3 h, 6%


Et3N,
TsN3
CH2Cl2
RT, 20 h, 80% (2 steps)


i-Bu2AlH
PhMe
-78 °C, 30 min



NH2NH2,
O2,
CuSO4
1 atm
EtOH, H2O
RT, 12 h, 88%
