Synthesis of Estrone

Structure of Estrone

C18H22O2

Principal investigatorK. Peter C. Vollhardt
Publication year1979
Synthesis typeTotal
Number of steps 9 (2 parts)
References
Part 1 of 2
intermediate structure
  1. n-BuLi , (CH2NMe2)2
  2. Ethylene oxide
THF
-40 °C, 60 min, 65%
intermediate structure
TsCl
Pyr
0 °C, 13 h
intermediate structure
NaI
Acetone
45 °C, 30 h, 95% (2 steps)
intermediate structure
Part 2 of 2
intermediate structure
  1. CuI , VinylMgBr
  2. Et3N , TMSCl , HMPA
THF
-60 °C to RT, 3 h, 89%
intermediate structure
Special reagent
LiNH2
NH3, THF
-45 to -35 °C, 9 h, 43%
intermediate structure
Special reagent
CpCo(CO)2
Reflux, 41 h
intermediate structure
Decane
Reflux, 20 h, 71% (2 steps)
intermediate structure
CF3CO2H
hv
CCl4, CHCl3
-60 to -10 °C, 20 h
"The product is a 90:10 mixture of regioisomers."
intermediate structure
Pb(OAc)4
CF3CO2H
-30 to -5 °C, 30 min, 88% (2 steps)
intermediate structure