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• W1476081805 abstract "Publisher Summary The oxoporphines can be divided into two distinct subgroups. The larger subgroup is made of weakly basic, nonphenolic compounds that are bright yellow or orange yellow in color. These are without exception high melting and usually show a decomposition point rather than an actual melting point. They possess a conjugated carbonyl function, so they show an IR absorption band near 1650 cm −1 . Additionally, these weakly basic, nonphenolic oxoaporphines turn red upon addition of acid, and their chloroform solutions show a greenish fluorescence. The smaller subgroup of oxoaporphines, which presently includes only the alkaloids PO-3 and corunnine, consists of high-melting, monophenolic, quaternary N-metho salts that are green in neutral or basic solution and red in acid. The oxoaporphine alkaloid pontevedrine possesses an N -methyl pyridone moiety. The lysicamine NMR spectrum was instructive because it showed methoxyl singlets at δ4.00 and 4.02, as well as the absence of a methylenedioxy signal. All aporphines and oxoaporphines are substituted at C-1 and C-2, so it was apparent that lysicamine must be 1,2-dimethoxyoxoaporphine. Conclusive proof of the structure was provided through a total synthesis. The NMR spectrum of corunnine in trifluoroacetic acid revealed three aromatic methoxyls—namely, (1) a quaternary N-methyl singlet, (2) an aromatic AB system assigned to the C-4 and C-5 protons, and (3) three aryl proton singlets. There is a claim that oxidation products derived from aporphines carrying a phenolic function at C-1 or C-11 are green, the phenolic function in corunnine was placed at C-1. This chapter also discusses some oxoaporphines not isolated from natural sources, such as 1,2,10,11-tetramethoxyoxoaporphine and 2,9,10-trimethoxyoxoaporphine etcetera. There are notes on biogenesis, pharmacology, ultraviolet spectroscopy, nuclear magnetic resonance (NMR) and mass spectroscopies." @default.
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• W1476081805 date "1973-01-01" @default.
• W1476081805 modified "2023-09-25" @default.
• W1476081805 title "Chapter 6 The Oxoaporphine Alkaloids" @default.
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• W1476081805 doi "https://doi.org/10.1016/s1876-0813(08)60223-7" @default.
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