Total synthesis of Quadrone (Yoshii):
| Reference: | Takeda, K.; Shimono, Y.; Yoshii, E. J. Am. Chem. Soc. 1983, 105, 563. DOI |
| Reactions: | Ketone → EnolSilane • Aldol-Na → Enone • Cyclopentenone • Alkyne → Ketone • Al-Allenyl/Propargyl+Ketone • Felkin-Anh • EnolSilane+Alkyl-X • Alkyl-X+Enolate • DeMayo cycloaddition • Photochemistry 2+2 • Cyclobutane • Bicyclo(420) • Wagner-Meerwein • Mechanism • Bicyclo(321) • Alkyl-OH → Ketone • O-Me → O-H • Alkyl-OH → CarboxAcid • Jones oxidation • CarboxAcid → CarboxEster • O-C(O)R → O-H • |
| Reagents: | Photochemistry • LiNiPr2 • Chloromethyl ether • Allenyl-AlR2 • Propargyl-Br • HgO • NaH • B(Br)3 • CrO3, H2SO4 (Jones) • Diazomethane • CH2I2, Zn/Cu • SiMe3-Cl • Acetone (solvent) • Formic acid • Hydroxide, sodium • CrO3Cl·PyH (PCC) • |