image

Total synthesis of Sordaricin:
Reference: Mander, L. N.; Thomson, R. J. Org. Lett. 2003, 5, 1321. DOI
Keywords: Ketone → Alkyl-OH • Ketone → Ketal • Retro-Diels-Alder → Alkene • Barton-McCombie reduction • Alkyl-OH → Alkyl-H • Claisen acylation, Mander • Enone enolate+Mander • Mander+enolate • O-MOM → O-H • Li-Nitrile+Alkyl-X • Alkyl-X+Enolate • Cu-Vinyl+Enone • ConjAdd Cu-R • Nitrile → Aldehyde • Alkyl-OH → Alkyl-I • Epoxide → Allyl-OH • Cu-Alkyl+Vinyl-X • Diels-Alder, Intram • Bicyclo(221) • EnolSilane → Ketone enolate • Ketone enolate+Me-I • Alkyl-X+Enolate • Retro-Diels-Alder → Alkene • Cu-Alkyl+Enone • Enone+Cu-R • ConjAdd-Alkylation • ConjAdd-Silylation • ConjAdd Cu-R • Allyl-OH → Enal • O-MOM → O-H • O-H → O-SiMe2tBu • Epoxidation, peracid • O-H → O-MOM • ConjAdd M-CN • Aldehyde → Alkyl-OH • O-H → O-MOM • CarboxEster → CarboxAcid • O-SiMe2tBu → O-H •
Reagents: Propenyl-MgX • BH4-Na+ • S=C(OPh)Cl • TsOH·Py • SiMe2tBu-Cl • Perbenzoic acid, 3-chloro • LiNiPrCy • Chloromethyl ether • I2 • Cyanide, potassium • Dowex • LiNiPr2, HMPA • AlHiBu2 • LiNiPr2 • MgBr2 • MnO2 • Thiolate, propyl • BH4-Na+ • Chloromethyl ether • O=C(OR)CN • HSnBu3 • AIBN • Fluoride, R4N+ • CuI • Thiol, n-butyl • LiCH2-OR • MeLi • SiMe3-Cl • CuI • HMPA (solvent) • Epoxide • Bicarbonate, sodium • NaH • Tf2NPh • Alkyl-MgX •

Syntheses Home