Total synthesis of Reiswigin A Model:
| Reference: | Jones, D. N.; Maybury, M. W. J.; Swallow, S.; Tomkinson, N. C.O.Tetrahedron Lett. 1993, 34, 8553. DOI |
| Reactions: | Li-Allyl+Ketone • Enone+Li-R • ConjAdd-Alkylation • KetoSulfone enolate+Alkyl-X • Alkyl-X+Enolate • Reductive elimination - S/OR • Allyl-OH → Enone • ConjReduct-Acylation • EneSulfone ConjReduct • Li-Sulfone+CarboxEster • Cycloheptane • Bicyclo(530) • Dehydration → Ene • Ketone enolate+Alkyl-X • Bromoacetate+Enolate • Epoxidation, peracid • Ketone → Alkyl-OH • |
| Reagents: | LiCHR-Sulfonyl • Allyl-Li • EneSulfone • Iodoacetate • NaH • MeI • AlH4-Li+ • SOCl2 • Na(Hg) • Permanganate, barium • LiCHR-Sulfonyl • Perbenzoic acid, 3-chloro • |