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Total synthesis of Sirenin:
Reference: Grieco, P. A. J. Am. Chem. Soc. 1969, 91,5660. DOI
Keywords: HWE → EnoateEster • Diazoketone Cyclopropanation • Cyclohexanone • CompRed-Ketone/CarboxEster+M-H • Mg-Allyl+Allyl-X • Hydroboration alkene • CompRed-Alkene/Alkene+M-H • Alkyl-OH → CarboxAcid • Diazoketone • Ozonolysis • Claisen acylation, formate • Ketone enolate+Formate • Enol → EnolEther • EnolEther → Enal • EnoateEster → Allyl-OH • CarboxAcid → CarboxCl •
Reagents: Allyl-MgX • NaH • BH(Siam)2 • H2O2, NaOH • CrO3, H2SO4 (Jones) • SOCl2 • Diazomethane • Me2S • HMPA (solvent) • HI • NaH • BH4-Na+ • HCl • AlH4-Li+ • HMPA (solvent) •

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