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Total synthesis of Tedanolide, 13-Deoxy- (Part 1):
Reference: Smith, A. B.; Adams, C. M.; Barbosa, S. A. L.; Degnan, A. P. J. Am. Chem. Soc 2003, 125, 350. DOI (Part 2) (Part 3)
Keywords: O-H → O-SiMe2tBu • CarboxAmide(Evans) → CarboxEster(thio) • CarboxEster(thio) → Aldehyde • CarboxAmide(Evans) → Alkyl-OH • Diol-1,3 → Acetal • O-SiMe2tBu → O-H • O-H → O-Me • Acetal → Ether • Alkyl-OH → Aldehyde • Alkyl-OH → Aldehyde • Corey-Fuchs • Li/H → Li-Alkynyl • Sn-Vinyl → I-Vinyl • Ketal → Diol-1,2 • O-H → O-SEM • Corey-Fuchs • Fritsch-Buttenberg-Wiechell • Aldol-B-Evans • Hydrostannation Alkyne • Li-Alkynyl+Alkyl-X • Allyl-OH → Enal • O-H → O-SiiPr3 • CarboxAmide(Evans) → Alkyl-OH • O-H → O-C(O)R • Alkene cleavage • O-C(O)R → O-H • O-H → O-C(O)R • O-PMB → O-H • Alkyl-OH → Aldehyde • O-C(O)R → O-H • Alkyl-OH → Alkyl-I • B-Allyl-Tartrate+Aldehyde • Aldol-B-Tartrate • Wittig-carboxymethyl → EnoateEster • Wittig-alkyl → Ene-cis • Aldol-B-Evans • Hydroboration alkene • CompRed-Alkene/Alkene+B-H • Hydrogenolysis Acyl-SR • CarboxEster(thio) → Aldehyde • Aldol-B-Evans • Lemieux-Johnson oxidation • O-H → O-SiiPr3 • Li/I → Li-Vinyl • Li-Vinyl+Aldehyde • Diol-1,2 → Ketal •
Reagents: Chiral auxiliary-Evans • BOTfBu2 • SiMe2tBu-OTf • Thiolate, ethyl • HSiEt3, Pd • Chiral auxiliary-Evans • BOTfBu2 • BH4-Li+ • Fluoride, R4N+ • MeI • AlHiBu2 • DMSO, Py·SO3 (Parikh-Doering) • DMSO, (COCl)2 (Swern) • PPh3=CBr2 • BuLi(n) • BuLi(tert) • HSnBu3 • I2 • TsOH·Py • Acetyl chloride • SEM-Cl • Carbonate, potassium • PdCl2 • MeI • Crotyl-B(tartrate) • Chiral auxiliary-Boronate • PPh3=C(Me)-CO2R • DMSO, (COCl)2 (Swern) • BOTfBu2 • SiEt2iPr-OTf • BH4-Li+ • Acetic anhydride • OsO4, NMO • Periodate, sodium • Carbonate, potassium • TsOH·Py • BH-BBN • Acetic anhydride, NEt3 • DDQ • Dess-Martin • PPh3=CH-Me • Carbonate, potassium • Iodide, phosphonium • H2O2, NaOH • BuLi(tert) • SiiPr3-OTf • Me2C(OMe)2

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