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 |
| Reactions: | Ketal → Diol-1,3 • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • Hydroboration → Alkyl-OH • Diels-Alder, Intram, Ene • Pyrone cycloaddition • Bicyclo(222)-oxa • CarboxEster → Aldehyde • O-C(O)R → O-H • O-H → O-SO2Me • Ether-4 • Bicyclo(420)-oxa • O-H → O-Bn • Diol-1,3 → Ketal • O-SiMe2tBu → O-H • O-H → O-C(O)R • |
| Reagents: | KH • AlH2(OR)2-Na+ • Me2C(OMe)2 • Sulfonic acid, Camphor • BH3 • Acetic anhydride • Sulfonic acid, Camphor • SiMe2tBu-OTf • Hydroxide, potassium • Sulfonyl chloride, methane • NaH • Fluoride, R4N+ • Iodide, R4N+ • B(OH)2Ph • Butadiene, 1-OR • Benzyl-X • |