Total synthesis of Prostaglandin E1:
| Reference: | Tanaka, T.; Toru, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Kurozumi, S.; Suzuki, M.; Kawagishi T.; Noyori, R. Tetrahedron Lett. 1983, 24, 4103-4104. DOI |
| Reactions: | Radical reduction(C-NO2) • Cu-Vinyl+Enone • ConjAdd-Michael • Ketone enolate+EneNitro • EneNitro+Enolate • O-SiMe2tBu → O-H • Enone → Allyl-OH (asym) • O-H → O-SiMe2tBu • Alkyl-NO2 → Alkyl-H • |
| Reagents: | HSnBu3 • AIBN • HF·Py • AlH(OEt)Binaphthol-Li+ • SiMe2tBu-Cl • EneNitro • PBu3 • Acetonitrile (solvent) • |