Abstract
The 1H nuclear magnetic resonance (NMR) chemical shifts and coupling constants of heroin's D ring H-15 alpha, H-15 beta, and H-16 alpha, and H-16 beta are presented. These assignments were accessible through the introduction of a double bond (delta 15,16) in heroin. The resulting compound, delta 15,16 didehydroheroin, was subjected to deuterium exchange or stereoselective reduction or both. Reduced products d1-16 alpha heroin d2-15 alpha, 15 beta-heroin, and d3-15 alpha, 15 beta, 16 alpha-heroin are presented. Heroin with deuterated acetyls is also presented for 1H NMR spectral clarity in the D ring area.
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