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
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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
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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%

