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Total synthesis of Digitoxigenin:
Reference: Stork, G.; West, F.; Lee, H. Y.; Isaacs, R. C. A.; Manabe, S. J. Am. Chem. Soc. 1996, 118,10660-10661. DOI
Keywords: Ketone → Alkyl-OH • Diol-1,2 cleavage • Li-PhosphineOxide+Aldehyde • Aldehyde+Li-Allyl • Ketal → Ketone • Ketone → Alkyl-OH • O-H → O-SiMe2tBu • Si-Alkynyl → H-Alkynyl • Epoxidation, peracid • Aldehyde → Oxime • Li-Alkyl+Nitrile • O-Bn → O-H • O-SiMe2tBu → O-H • Ketone → Ketone-α-OR • Diol-1,2 cleavage • Aldehyde → Alkyl-OH • CompRed-Aldehyde/Aldehyde+B-H • HWE → Diene • Aldehyde → Alkyl-OH • HWE → EneSulfide • Diels-Alder, EneSulfide • Mitsunobu → Ester • Ketall(thio) → Ketone • Ketone+Mg-Alkyl • Pinacol • Aldehyde → Nitrile • Nitrile epimerization • Nitrile+Li-R → Ketone • Li-Ether+Nitrile • Lactone-5 • Alkene isomerization •
Reagents: SiMe3-Cl • Me2S • BH4-Na+ • Periodate, sodium • BH(OAc)3-Na+ • Allyl-Li • HMPA (solvent) • DMSO, (COCl)2 (Swern) • BuLi(n) • HCl, H2O • BH4-Na+, CeCl3 • PPh3 • DEAD • Acetic acid, trifluoro • Me3O+ X- • NaOEt • Alkyl-MgX • Fluoride, R4N+ • HSnBu3 • AIBN • Perbenzoic acid, 3-chloro • BF3·OEt2 • NH2OH • O=C(Imid)2 • LiCH2-OR • LiNEt2 • BHT • H2, Pd • PPh3=C=C=O • NEt3 • TsOH •

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