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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. DOI
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 • Acetic acid, trifluoro • O3 • Hydroxide, sodium • Alkynyl-Li • Zn° •

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