Total synthesis of Scalarenedial:
| Reference: | Corey, E. J.; Luo, G.; Lin, L. S. J. Am. Chem. Soc. 1997, 119, 9927. DOI |
| Reactions: | O-H → O-C(S)OR • Cationic cyclization • Silyl ketone alkylation • Ketone azaenolate+Alkyl-X • Alkyl-X+Azaenolate • Barton-McCombie reduction • Alkyl-OH → Alkyl-H(2°) • Si-Alkyl → HO-Alkyl • Pd-Carboxylation • EnolTriflate → EnoateEster • Lactone-5 • Mechanism • Ketone → EnolTriflate • Brook rearrangement • Li-Sulfone+Ketone • CompE+-Ketone-Si/Epoxide+M-R • Mechanism • Cyclohexane • Cyclohexanone • Bicyclo(440) • Lactone → Lactol • Allyl-OH → Enal • |
| Reagents: | Allyl-Br • AlMe2-Cl • S=C(OC6F5)Cl • Tf2NPh • BF3 • Pd(OAc)2 • AlHiBu2 • Hydroxide, potassium • DMSO, (COCl)2 (Swern) • KN(SiMe3)2 • H2O2 • HSnBu3 • DMAP • NEtiPr2 • CO • Silyl ketone • LiCHR-Sulfonyl • |