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Total synthesis of Sirenin:
Reference: Corey, E.J.; Achiwa, K.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 4318. DOI
Keywords: O-C(O)OR → O-H • O-H → O-THP • CarboxEster → Alkyl-OH • O-THP → O-H • Allyl-OH → Allyl-Br • Hydrogenation Alkyne • Alkyl-OH → Aldehyde • Aldehyde → CarboxAcid • CarboxAcid → CarboxCl • Diazoketone • Ozonolysis • CompOx-Alkene/Alkene+O3 • HWE → EnoateEster • Li-Alkynyl+Alkyl-X • Alkyl-X+Li-R • Claisen acylation, carbonate • Ketone enolate+Carbonate • Ketoester → Enone • CarboxEster → Alkyl-OH • Diazoketone Cyclopropanation •
Reagents: O3 • Zn° • Carbonate, potassium • DHP • AlCl3 • Benzoyl chloride, 2,4,6-trimethyl • Pyridine • TsOH • PBr3 • Alkynyl-Li • TsOH • H2, Ni • CrO3·Py2 (Collins) • Ag2O • Oxalyl chloride • Diazomethane • O=C(OR)2 • NaH • BH4-Na+ • Benzoyl chloride • KOtBu • AlCl3 • CuSO4

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