Synthesis of Pentacycloanammoxic Acid

Structure of Pentacycloanammoxic Acid

C20H30O2

Principal investigatorElias J. Corey
Publication year2004
Synthesis typeTotal
Number of steps 15 (linear)
References
Part 1 of 1
intermediate structure
Br2
intermediate structure
DBAD
intermediate structure
H2, PtO2, NaNO2
EtOH, THF
RT
intermediate structure
Zn
AcOH
95 °C, 60 min, 80% (2 steps)
intermediate structure
2-Cyclopentenone
MeCN
RT, 12 h, 40%
intermediate structure
  1. H2
  2. Pd/C
  3. O2
EtOH
RT, 2.5 h, 76%
intermediate structure
HC(OMe)3, TsOH
MeOH
40 °C, 60 min, 91%
intermediate structure
AcOH
MeCN, H2O
50 °C, 3 h, 6%
intermediate structure
HCO2Et, NaOMe
PhH
RT, 12 h
intermediate structure
TsN3, Et3N
CH2Cl2
RT, 20 h, 80% (2 steps)
intermediate structure
Et3N
MeOH
RT, 3 h, 72%
intermediate structure
i-Bu2AlH
PhMe
-78 °C, 30 min
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 6 d, 91% (2 steps)
See the Swern Oxidation
intermediate structure
Ph3P(CH2)6CO2H+ Br-, i-Pr2NLi
THF
-78 °C to RT, 7.5 h, 67%
See the Wittig Reaction
intermediate structure
NH2NH2, CuSO4, O2
EtOH, H2O
RT, 12 h, 88%
intermediate structure