Volume 30, Issue 3 (July 1985)
1H Nuclear Magnetic Resonance of Heroin's D Ring
The 1H nuclear magnetic resonance (NMR) chemical shifts and coupling constants of heroin's (1) D ring H-15α, H-15β, and H-16α, and H-16β are presented. These assignments were accessible through the introduction of a double bond (Δ15,16) in heroin. The resulting compound, Δ15,16 didehydroheroin (2), was subjected to deuterium exchange or stereoselective reduction or both. Reduced products d1-16αheroin (3), d2-15α, 15β-heroin (4), and d3-15α, 15β, 16α-heroin (5) are presented. Heroin with deuterated acetyls is also presented for 1H NMR spectral clarity in the D ring area.