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Adlumidiceine

Bicuculline (88) Erythro Aobamidine (96) Z Adlumidiceine Bicucullinine Fumaramine Z... [Pg.263]

The secophthalideisoquinoline enol lactones may exist as Z or geometric isomers. Three pairs of such isomers are known aobamidine (96) (Z) and adlumidiceine enol lactone (97) ( ), /V-methylhydrastine (98) (Z) and (E)-N-methylhydrastine (99) ( ), (Z)-narceine enol lactone (101) and ( )-narceine enol lactone (102). Three of these enol lactones (99, 101, 102) are synthetic products. Lists of these alkaloids, the plant species in which they occur, as well as their spectral data and other references are provided in the review papers (4,5,8). Narceine enol lactones (101 and 102) are described in Refs. 87 and 90. [Pg.265]

The enol lactones were synthesized by Hofmann degradation of metho salts of classic phthalideisoquinoline alkaloids. The biogenetically relevant transformations were highly stereospecific. In this way aobamidine (96) was obtained from the methiodide of (erythro) bicuculline (88) (2), and ad-lumidiceine enol lactone (97) was produced from both (threo) isomeric adlumidiceine (89) and capnoidine (90) methiodides (14,15,91-93). (Z)- (98) and ( )-N-methylhydrastine (99) were obtained from / - (91, erythro) and a-N-methylhydrastinium (92, threo) iodides (5,87,91,96-98), respectively, as were (Z)- (101) and (JE)-narceine enol lactones (102) synthesized from a- (94, erythro) and /J-narcotine (95, threo) quaternary N-metho salts (87,90), respectively. In a similar process /J-hydrastine (91) JV-oxide heated in chloroform yielded enol lactone 124 of Z configuration (99) however, a-narcotine (94) N-oxide was transformed to benzoxazocine 125 (99). ... [Pg.267]

Enol lactones can also be obtained from keto acids by enolization-dehydration. Adlumidiceine (103) as well as N-methylhydrasteine (104) when heated in toluene with acetic anhydride or p-toluenosulfonic acid were transformed to enol lactones 97 (97) and 98 (5,102), respectively. Narceine (106) under the influence of PC13 yielded 101 (87,100). [Pg.267]

Potassium permanganate oxidizes both adlumidiceine (103) and ad-lumiceine (105) to the corresponding diketo acids bicucullinine (108) and bicucullinidine(llO), respectively (/13). Air oxidation of N-methylhydrasteine (104) leads to the expected N-methyloxohydrasteine (109) as well (J). Another way of transforming the keto acids (e.g., 104) to diketo acids (e.g., 109) utilizes the isonitroso derivatives (e.g., 133), which on hydrolysis gives the diketone (102). [Pg.270]

Bicucullinine (108) was synthesized by Nalliah and MacLean (41) from N-methyldehydrobicucullinium salt (143) by Hofmann degradation preceded by hydrolysis and air oxidation (Scheme 25). Bicucullinine (108), bicucullinidine (110), and N-methyloxohydrasteine (109) were prepared from the corresponding keto acids, adlumidiceine (103), adlumiceine (105), and N-methylhydras-teine (104), respectively, by oxidation with potassium permanganate (108 and 110) (113) or by air oxidation (109) (5). In another partial synthesis N-methyloxohydrasteine (109) was obtained from monoketo acid 104 by isonitrosation followed by hydrolysis (102). [Pg.273]

In the seco-phthalide-isoquinoline series the benzil derivatives bicucullinidine (278, R =R =Me) and bicucullinine (278, R R -CHa) have been prepared by oxidation of the deoxybenzoin alkaloids adlumiceine and adlumidiceine (Kh.Kiryakov and Mard-irosyan, Dokl.Bolg.Akad.Nauk, 1981, 1717), the analogue... [Pg.318]

Adlumidiceine, apocavidine, berberine, bulbocapnine, canadine, capnotdine, coptisine, corybulbine, corycavamine, 50, 72-77... [Pg.391]

Adlumidiceine. berberine, bicuculline, copcisine. oorypalmine, corysamine, enol lactone at adlumidiceine. isocorydine, 73, 111, 112... [Pg.392]

Adlumiceine, enol lactone of adlumiceine, adlumidiceine, (-)- dlumine, bicucine, bicuculline, capnoidine, coptisine, 73, 140... [Pg.392]

The presence of narcotine as well as of a number of other isoquinoline alkaloids in the aerial parts of Papaver fugax of Turkish origin has been established. Adlumidiceine (174 R + = CH2), adlumiceine (174 R = R = Me), and... [Pg.158]

Adiumiceine (341), adlumidiceine (340), adlumidiceine enol lactone (337, trans), adlutnine (326), berberine (209b), bicuculline (325), capnoidine (325), coptisine (217b), cryptopine (311), oxysanguinarine (281), protopine (309) (186)... [Pg.57]

Adlumiceine, adlumiceine enol lactone, adlumidiceine, adlumidiceine enol lactone, aobamidine, bicucullinine, fumaramine, Al-methylhydrasteine, Al-methylhydrastine... [Pg.59]

Adlumidiceine enol lactone (337) Aobamidine (= adlumidiceine enol lactone) (337, cis)... [Pg.88]

See other pages where Adlumidiceine is mentioned: [Pg.263]    [Pg.269]    [Pg.34]    [Pg.34]    [Pg.142]    [Pg.142]    [Pg.313]    [Pg.135]    [Pg.154]    [Pg.155]    [Pg.479]    [Pg.480]    [Pg.158]    [Pg.9]    [Pg.12]    [Pg.12]    [Pg.52]    [Pg.54]    [Pg.60]    [Pg.61]    [Pg.61]    [Pg.88]    [Pg.427]    [Pg.307]    [Pg.28]   
See also in sourсe #XX -- [ Pg.269 ]

See also in sourсe #XX -- [ Pg.313 , Pg.318 ]

See also in sourсe #XX -- [ Pg.391 , Pg.392 , Pg.395 , Pg.479 , Pg.480 ]

See also in sourсe #XX -- [ Pg.12 ]

See also in sourсe #XX -- [ Pg.427 ]

See also in sourсe #XX -- [ Pg.307 ]



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Adlumidiceine enol lactone

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