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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
Keywords: 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 • BINAL-H • SiMe2tBu-Cl • Acetonitrile (solvent) •

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