Synthesis of Mycophenolic Acid

Structure of Mycophenolic Acid

C17H20O6

Principal investigatorRick L. Danheiser
Publication year1986
Synthesis typeTotal
Number of steps 9 (linear)
References
J. Am. Chem. Soc. 1986, 108, 806.
Part 1 of 1
intermediate structure
NaBH4
EtOH
0 °C to RT, 30 min
intermediate structure
DMAP, Et3N, TBSCl
CH2Cl2
RT, 20 h
intermediate structure
K2CO3
MeOH
RT, 24 h, 83% (2 steps)
intermediate structure + intermediate structure
  1. MsCl , n-BuLi
  2. Li2CuCl4
THF
-78 °C to RT, 8 h, 91%
intermediate structure + intermediate structure
Sealed tube
PhH
120 °C, 14 h, 73%
See the Danheiser Benzannulation
intermediate structure
t-BuNH2, Br2
PhMe
-78 to 5 °C, 4 h, 85%
intermediate structure
  1. MeLi.LiBr
  2. t-BuLi
  3. CO2
THF
-78 to 0 °C, 2.5 h
intermediate structure
HCl
H2O, MeOH
Reflux, 4.5 h, 70% (2 steps)
intermediate structure
CrO3, H2SO4
Acetone, H2O
-30 °C, 5 h, 61%
See the Jones Oxidation
intermediate structure
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