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Total synthesis of 4-Androstene-3,17-dione:
Reference: Schmidt, R.; Huesmann, P. L.; Johnson, W. S. J. Am. Chem. Soc. 1980, 102, 5122.
Keywords: Acetal -> Aldehyde --- CarboxEster -> Alkyl-OH --- Alkyl-OH -> Aldehyde --- Ketal -> Ketone --- Li-Me+Enone --- Claisen-Johnson --- Cationic cyclization --- Si-Propargyl+Carbenium --- Li-Alkynyl+Alkyl-X --- Wittig-alkyl -> Ene-trans --- Aldol-Na -> Enone --- Mg-Vinyl+Aldehyde --- Mechanism --- Ozonolysis --- Li-Alkynyl+Alkyl-X --- Steroid synthesis
Reagents: NaNH2 --- SiMe3-CH2Cl --- HCl, H2O --- Vinyl-MgX --- Orthoacetate --- AlH4-Li+ --- Cr2O7·2PyH (PDC) --- Ph3P=CH-Alkyl --- PhLi --- HCl, H2O --- Hydroxide, sodium --- MeLi --- CF3CO2H --- O3 --- Hydroxide, sodium --- Alkynyl-Li --- Zn°

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