Total synthesis of Prelog-Djerassi Lactonic Acid:
| Reference: | Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807-810. DOI |
| Reactions: | O-SiMe3 → O-H • CarboxAmide enolate(Evans)+Alkyl-X • Allyl-X+Enolate (asym) • Aldol-B-Evans • Carboxamide enolate+Aldehyde (asym) • Alkyl-OH → CarboxAcid • Lactone-6 • CarboxAmide(Evans) → CarboxAcid • CarboxAmide(Evans) → Alkyl-OH • Alkyl-OH → Aldehyde • O-H → O-SiMe3 • Hydroboration → Alkyl-OH • CompRed-Alkene/Carboxamide+M-H • |
| Reagents: | LiNiPr2 • Allyl-I • AlH4-Li+ • DMSO, Py·SO3 (Parikh-Doering) • DMAP • BH2(Thexyl) • H2O2 • Oxalic acid • NMO • PPh3 • Hydroxide, lithium • Chiral auxiliary (amide-Evans) • Chiral auxiliary (amide-Evans) • |