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Total synthesis of Taxol Ring D:
Reference: Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Pai, W. M.; Guy, R. K. Chem. Commun. 1992, 1118. DOI
Keywords: O-H -> O-Bn • CarboxEster -> Aldehyde • Diol -> Ketal • O-H -> O-C(O)R • Ketal -> Diol • O-H -> O-SiMe2tBu • O-C(O)R -> O-H • O-H -> O-SO2R • Ether-4 • O-SiMe2tBu -> O-H • Hydroboration Alkene • Diels-Alder, tethered •
Reagents: KH • AlH2(OR)2-Na+ • Me2C(OMe)2 • Camphor sulfonic acid • BH3 • Acetic anhydride • Camphor sulfonic acid • SiMe2tBu-OTf • Hydroxide, potassium • MeSO2Cl • NaH • Fluoride, Bu4N+ • Iodide, Bu4N+ • PhB(OH)2

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