Total synthesis of Sordaricin:
| Reference: | Mander, L. N.; Thomson, R. J. Org. Lett. 2003, 5, 1321. DOI |
| Reactions: | Ketone → Alkyl-OH • Ketone → Ketal • Retro-Diels-Alder → Enone • Barton-McCombie reduction • Alkyl-OH → Alkyl-H • Claisen acylation, Mander • Enone enolate+Mander • Mander+enolate • O-MOM → O-H • Nitrile anion+Alkyl-X • Cu-Vinyl+Enone • ConjAdd Cu-Vinyl • Mg-R → Cu-R • Nitrile → Aldehyde • Alkyl-OH → Alkyl-I • O-SiMe2tBu → O-H • Epoxide → Allyl-OH • Cu-Alkyl+Vinyl-X • ConjAdd-Elimination • ConjAdd Cu-Alkyl • Mg-R → Cu-R • Diels-Alder, Intram, Ene • Bicyclo(221) • Bicyclo(321) • EnolSilane → Ketone enolate • Ketone enolate+Me-I • Alkyl-X+Enolate • Retro-Diels-Alder → Enone • Cu-Alkyl+Enone • Enone+Cu-R • ConjAdd-Alkylation • ConjAdd-Silylation • ConjAdd Cu-Alkyl • Allyl-OH → Enal • O-MOM → O-H • O-H → O-SiMe2tBu • Epoxidation, peracid • O-H → O-MOM • ConjAdd M-CN • Cyanide+Enone • Aldehyde → Alkyl-OH • O-H → O-MOM • CarboxEster → CarboxAcid • Ketal → Ketone • |
| Reagents: | Propenyl-MgX • BH4-Na+ • S=C(OPh)Cl • TsOH·Py • SiMe2tBu-Cl • 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 • Me-Li • SiMe3-Cl • CuI • Epoxide • Bicarbonate, sodium • NaH • Tf2NPh • Alkyl-MgX • TsOH • Perbenzoic acid, 3-chloro • |