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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: CarboxEster → Aldehyde • Diol-1,3 → Ketal • O-H → O-C(O)R • Ketal → Diol-1,3 • O-H → O-SiMe2tBu • O-C(O)R → O-H • O-H → O-SO2R • Ether-4 • O-SiMe2tBu → O-H • Hydroboration alkene • Diels-Alder, Intram • O-H → O-Bn •
Reagents: KH • AlH2(OR)2-Na+ • Me2C(OMe)2 • Camphor sulfonic acid • BH3 • Acetic anhydride • Camphor sulfonic acid • SiMe2tBu-OTf • Hydroxide, potassium • Sulfonyl chloride, methane • NaH • Fluoride, R4N+ • Iodide,R4N+ • PhB(OH)2 • Benzyl-X •

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