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Total synthesis of Pleuromutilin Fragment:
Reference: Paquette, L. A.; Wiedeman, P. E.; Bulman-Page, P. C. J. Org. Chem. 1988, 53, 1441. DOI
Keywords: Acetoacetic ester synthesis • Lactone enolate+Aldehyde • Dehydration → EneLactone • Ketone+Mg-Alkynyl • CompE+-Ketone/CarboxEster+M-R • Alkyl-OH → Aldehyde • CompOx-Alkyl-OH/Sulfide+CrO3 • Lactol → Lactone • CompOx-Lactol/Alkyl-OH+CrO3 • Lactone-5 • Lactone enolate+Aldehyde • Reductive elimination - Se/OR • Lactone enolate+Alkyl-X • Deconjugative alkylation • Alkyl-X+Enolate • Nazarov • Mechanism • Cyclopentanone • Enone → Ketal(thio) • Enone → Ketal(thio) • CarboxEster → Alkyl-OH • Mg-Alkyl+Aldehyde • Acetal → Aldehyde •
Reagents: NaH • MeI • Alkynyl-MgX • Thiol, (CH2)2-SH • AlHiBu2 • TsOH • CrO3·Py2 (Collins) • CrO3, H2SO4 (Jones) • TsOH • Thiol, (CH2)2-SH • TsOH • TsOH • LiNiPr2 • Acetaldehyde • Sulfonyl chloride, methane, NEt3 • DBU • LiNiPrCy • MeI • HMPA (solvent) • LiNiPr2 • MeI • LiNiPr2 • Phenylselenoacetaldehyde • Sulfonyl chloride, methane, NEt3 • H2SO4 • HMPA (solvent) •

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