- Synthesis of neopine and its 5β- and 7-substituted derivatives (chemistry of opium alkaloids, part XL)
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Heating 14β-bromocodeine (3) with methanol and triethylamine yielded 6α,7α-epoxy-6-deoxyneopine (5).The epoxide 5 was reduced to neopine (7) with lithium aluminium hydride, whereas reaction of 5 with sodium methoxide gave 7β-methoxyneopine (9).Similar reactions were performed with 14β-bromo-5β-methylcodeine (4), yielding the corresponding 5β-methyl derivatives 6, 8 and 10.Acetylation of 3 and 4 gave 6α-O-acetyl-14β-bromocodeine (11) and its 5β-methyl analogue 12, respectively, from which the ortho esters 13 and 14 were obtained after treatment with methanol.Acid hydrolysis of 13 or, better, solvolysis of 11 in water yielded a mixture of 6α-O-acetyl-7α-hydroxyneopine (15) and 7α-acetoxyneopine (17).Under the same conditions 12 and 14 gave the 5β-methyl analogues 16 and 18.
- Meuzelaar, G. J.,Woudenberg, R. H.,Sinnema, A.,Maat, L.
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Read Online
- BIOTRANSFORMATION OF THEBAINE BY CELL SUSPENSION CULTURES OF PAPAVER SOMNIFERUM CV. MARIANNE
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Thebaine is biotransformed to neopine by cell suspension cultures of Papaver somniferum cv.Marianne grown in O-B5 medium.Results of precursor studies on these cell suspension cultures are also described.Key Word Index - Papaver somniferum; Papaveraceae; cell suspension culture; biotransformation; thebaine; neopine; morphinan alkaloids.
- Tam, W. H. John,Kurz, Wolfgang G. W.,Constabel, Friedrich,Chatson, Kenneth B.
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Read Online
- Compositions and Methods For Making Alkaloid Morphinans
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Methods that may be used for the manufacture of a class of chemical compounds known as morphinans, including neopine, are provided. Compositions useful for the synthesis of morphinans, including neopine, are also provided.
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Paragraph 0051; 0236-0238
(2017/09/30)
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- METHOD FOR THE CATALYTIC PRODUCTION OF HYDROCODONE AND HYDROMORPHONE
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A method for the catalytic conversion of codeine, morphine or analogs thereof into hydrocodone, hydromorphone or analogs thereof utilizing a transition metal complex of a tertiary phosphine halide as catalyst.
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Page/Page column 7
(2008/06/13)
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- NEODIHYDROTHEBAINE AND BRACTAZONINE, TWO DIBENZAZONINE ALKALOIDS OF PAPAVER BRACTEATUM
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Two new dibenzazonine alkaloids, neodihydrothebaine and bractazonine were isolated from Papaver bracteatum.Their possible biosynthesis from thebaine is discussed.The structures of both new alkaloids are proven by synthesis.An isomeric dibenzazonine compound was also prepared. - Keywords: Papaver bracteatum; Papaveraceae; alkaloids; dibenzazonines; neodihydrothebaine; bractazonine; biosynthetic pathway; synthesis; 5,6,8,9-tetrahydro-2-methoxy-7-methyl-dibenzazonin-1,12-diol; 5,6,8,9-tetrahydro-2,10-dimethoxy-7-methyl-dibenzazonin-1-ol; 5,6,8,9-tetrahydro-2,11-dimethoxy-7-methyl-dibenz-azonin-1-ol; 5,6,8,9-tetrahydro-2,12-dimethoxy-7-methyl-dibenzazonin-1-ol.
- Theuns, Hubert G.,Lenting, Herman B. M.,Salemink, Cornelis A.,Tanaka, Hitoshi,Shibata, Masayoshi,et al.
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p. 1157 - 1166
(2007/10/02)
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- Conversions of tosyl and mesyl derivatives of the morphine group, XX. Synthesis of mesyl esters
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A simple and convenient method had been developed for the preparation of dihydro derivatives of morphine alkaloids. In this was, 3-O-ethyldihydromorphine was obtained in crystalline form. This compound is described in the literature as an oily product. Several 6-O-mesyl derivatives have been synthesized in good yields also on a larger scale from the dihydro compounds by the use of Crossland's method.
- Makleit,Berenyi,Bognar,Elek
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p. 161 - 163
(2007/10/10)
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