Synthesis of Progesterone
C21H30O2
Principal investigator | William S. Johnson |
---|---|
Publication year | 1971 |
Synthesis type | Total |
Number of steps | 18 (3 parts) |
References |
Part 1 of 3
+
n-BuLi
THF
-60 °C to RT, ON, 73%
(CH2OH)2,
TsOH,
Hydroquinone
Dean-Stark
PhH
Reflux, 43 h, 71% (88% BRSM)
Ph3P
PhH
80 °C, 11 h, 94%
Part 2 of 3
+
NaOEt
EtOH
Reflux, 4.5 h
KOH
Ethylene Glycol, EtOH, H2O, 2-Methoxyethanol
80 to 135 °C, 5 h
Red-Al
PhH, THF
-70 °C, 6 h
Red-Al
PhH, THF
-70 °C, 6 h, 85%
Part 3 of 3
+
HCl
H2O, MeOH
40 °C, 6 h
MeLi
Et2O
RT, 2 min, 99%
Ethylene carbonate,
CF3CO2H
DCE
0 °C, 3 h, 71%
"The product is a 83:17 mixture of diastereomers at C-17 (major shown)"
- O3
- AcOH , Zn
CH2Cl2, MeOH
-70 to -15 °C, 32 min, 88%