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Total synthesis of Tetronolide (Part 3) New:
| Reference: | Boeckman, R. K. Jr.; Shao, P.; Wrobleski, S. T.; Boehmler, D. J.; Heintzelman, G. R.; Barbosa, A. J. J. Am. Chem. Soc. 2006, 128, 10572-10588. DOI (Part 1) (Part 2) |
| Reactions: | O-SiPh2tBu → O-H • O-MOM → O-H • Retro-Diels-Alder → Ketene • Ketene synthesis • Diels-Alder, Intram, Ene • Bicyclo(440) • Claisen acylation, acyl-X • Enol → EnolEther • Alkyl-OH → Aldehyde • Mg-Vinyl+Aldehyde • Li-R → Mg-R • EnolEther → Enal • O-PMB → O-H • Alkyl-OH → Alkyl-Cl • Alkyl-X → Alkyl-SO2R • Na-Sulfone+Aldehyde • Aldehyde+Na-R • Ketone-α-S(O)nR → Ketone • Enone → Allyl-OH • O-MOM → O-H • Alkyl-OH → Aldehyde • Ketene+Alcohol • O-H → O-C(O)R • Alkyl-OH → Ketone • |
| Reagents: | BHT • TsOH·Py • NaN(SiMe3)2 • HMPA (solvent) • Diazomethane, silyl • Dess-Martin • Vinyl-MgX • BuLi(tert) • Acetic acid, trifluoro • MgBr2 • Acetic anhydride, trifluoro • DDQ • Sulfinate, benzene • NaOtAm • DMSO, (CF3CO)2O • Al(Hg) • BH(sBu3)-Li+ • Chloromethyl ether • NEtiPr2 • TASF • Dess-Martin • HCl, MeOH • BHT • |