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Total synthesis of Scalarenedial:
Reference: Corey, E. J.; Luo, G.; Lin, L. S. J. Am. Chem. Soc. 1997, 119, 9927. DOI
Keywords: O-H → O-C(S)OR • Lactone → Lactol • Cationic cyclization • Silyl ketone alkylation • Ketone azaenolate+Alkyl-X • Alkyl-X+Azaenolate • Barton-McCombie reduction • Alkyl-OH → Alkyl-H • Si-Alkyl → HO-Alkyl • Allyl-OH → Enal • Pd-Carboxylation • EnolTriflate → EnoateEster • Mechanism • Ketone → EnolTriflate • Brook elimination • CompE+-Ketone-Si/Epoxide+Li-R • Mechanism •
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, KHCO3 • HSnBu3 • DMAP • NEtiPr2 • CO • Silyl ketone • LiCHR-Sulfonyl •

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