Total synthesis of Kromycin:
| Reference: | Boeckman, R. K. Jr.; Pruitt, J. R. J. Am. Chem. Soc. 1989, 111, 8286–8288. DOI |
| Reactions: | Li-Phosphonate+CarboxEster • O-H → O-SiEt3 • Ketone enolate+CO2 • KetoAcid → Ketal • Phosphonite → Phosphonate • Sharpless epoxidation • Payne rearrangement • Epoxide+M-SR • Sulfide → Sulfoxide • Pummerer • HWE → Enone • Ketone → Ketal(thio) • O-SiEt3 → O-H • Alkyl-OH → Aldehyde • CompOx-Alkyl-OH/Sulfide+DMSO • HWE → EnoateEster • Ketal(thio) → Ketone • Ketal → Diol-1,2 • CompNu-Ketal/Ketal+H+ • Retro-Diels-Alder → Ketene • Ketene+Alcohol • Lactone-9+ • |
| Reagents: | Hydroperoxide, tbutyl - Ti • Me2C(OMe)2 • Hydroxide, potassium • Amberlyst • Perbenzoic acid, 3-chloro • Acetic anhydride, trifluoro • Lutidine • HgCl2 • Carbonate, calcium • LiCH2-PO(OMe)2 • BuLi(n) • KOtBu • SiEt3-Cl • ZnI2 • Fluoride, R4N+ • DMSO, (COCl)2 (Swern) • NEt3 • CO2 • Iodide, sodium • MgCl2 • NEt3 • Vinyl-OAc • H2SO4 • LiNiPr2 • P(OEt)2Cl • H2O2 • KOtBu • TlNO2 • |