Total synthesis of Pentenomycin I (Smith):
| Reference: | Branca, S. J,; Smith, A. B. J. Am. Chem. Soc. 1978, 100, 7767. DOI |
| Reactions: | CarboxEster → Alkyl-OH • Ketal → Enone • O-SiMe2tBu → O-H • Enone → Enone-α-Halo • Ketone → Enone • Li-Vinyl+Aldehyde • Aldehyde+Li-Vinyl • Ketal → Enone • Ketone → Ketone-α-SeR • Selenoxide-Ei → KetoEsterEnone • KetoEster → Enone • Enone → Ketal • O-H → O-SiMe2tBu • Alkene → Diol-1,2 • Enone → Ketal • Li/Br → Li-Vinyl • |
| Reagents: | Br2 • NEt3 • Glycol • Vinyl-Li • Glycol • AlHiBu2 • BuLi(n) • Formaldehyde • SiMe2tBu-Cl • OsO4 • SeO2 • Acetic acid • Imidazole • TsOH • NaH • SePh-Cl • H2O2 • |