Synthesis of Estrone

Structure of Estrone

C18H22O2

Principal investigator	K. Peter C. Vollhardt
Publication year	1979
Synthesis type	Total
Number of steps	9 (2 parts)
References	J. Am. Chem. Soc. 1979, 101, 215. J. Am. Chem. Soc. 1980, 102, 5253. J. Am. Chem. Soc. 1976, 98, 6755.

Part 1 of 2

intermediate structure

n-BuLi , (CH2NMe2)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)

See the Finkelstein Reaction

intermediate structure

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Part 2 of 2

intermediate structure

CuI , VinylMgBr
Et3N , TMSCl , HMPA

THF

-60 °C to RT, 3 h, 89%

See the Michael Addition

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)

See the Diels-Alder Reaction

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

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