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Total synthesis of Steganacin:
Reference: Kende, A. S.; Liebeskind, L. L. J. Am. Chem. Soc. 1976, 98,267-268. DOI
Keywords: Malonic Ester Synthesis • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Malonic Ester Synthesis • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Oxidative coupling aryl-aryl • Cyclooctane • Benzylic oxidation → Benzyl-Br • Wohl-Ziegler bromination • Benzyl-Br → Benzyl-OH • Aldol-Na → Aldol • Ketone enolate+Aldehyde • Lactone-5 • CarboxEster → CarboxAcid • Decarboxylation malonic • O-H → O-SO2R • Alkyl-OH → Ketone • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • O-H → O-C(O)R •
Reagents: Sulfonyl chloride, methane, NEt3 • Malonate • NaH • VOF3 • Acetic anhydride, trifluoro • NBS • AgOCOCF3 • NEt3 • CrO3·Py2 (Collins) • Hydroxide, potassium • Formaldehyde • Hydroxide, potassium • BH4-Na+ • Acetic anhydride, Py •

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