image

Total synthesis of De-A-Quassimarin:
Reference: Kawabata, T.; Grieco, P. A.; Sham, H.-L.; Kim, H.; Jaw, J. Y.; Tu, S. J. Org. Chem. 1987, 52, 3346 DOI
Keywords: O-H -> O-Me • Ketone -> Enolsilane • Ketone -> Ketone-α-SeR • Ketone -> Enolsilane • Enolsilane -> Ketone-α-Halo • Hydroboration Alkene • O-H -> O-SiMe2tBu • Alkyl-OH -> Ketone • O-SiMe2tBu -> O-H • Alkyl-OH -> Aldehyde • Aldehyde -> CarboxAcid • Ketal -> Ketone • Lactone-6 • O-H -> O-MOM • Ketone -> Enolsilane • Saegusa oxidation • Enone -> Ketal(thio) • O-H -> O-MOM • O-MOM -> O-H • Allylic oxidation -> Enone • Enone enolate+Alkyl-X • ConjReduct Enone • Selenoxide-Ei -> Enone-6 • ConjAdd Cu-R • Cu-Vinyl+Enone • Ketone -> Ketone-α-Halo • Ketone -> Alkene • Shapiro reaction • Epoxidation, peracid • Ketal(thio) -> CH2 • Iodolactonization • Lactone-6 • Alkyl-X -> Alkyl-H • Radical reduction(C-I) • Lactone -> Lactone-α-OH • Ether-5 •
Reagents: MeI • CrO3·Py2 (Collins) • LiNiPr2 • MeI • Li°/NH3 • NH(SiMe3)2 (HMDS) • SiMe3-I • SePh-Cl • H2O2 • Vinyl-Li • CuI • PBu3 • NH(SiMe3)2 (HMDS) • SiMe3-I • NBS • DMF (solvent) • BH3 • H2O2, NaOH • DMAP • CrO3·Py2 (Collins) • Perbenzoic acid, 3-chloro • Fluoride, Bu4N+ • Hydrazine, tosyl • LiNiPr2 • CrO3·Py2 (Collins) • Ag2O • TsOH • Cl-CH2-OR • NH(SiMe3)2 (HMDS) • SiMe3-I • Pd(OAc)2 • HS-(CH2)2-SH • BF3·OEt2 • RaNi • Hydroxide, sodium • NEtiPr2 • Cl-CH2-OR • Hydroxide, sodium • I2 • HSnBu3 • AIBN • LiNiPr2, HMPA • MoOPH • Me2S • BF3·OEt2

Syntheses Home