Tropane alkaloid

Steroidal Alkaloids and Steroidal Glycoalkaloids Norditerpenoid Alkaloids Pyrrolizidine Alkaloids Indolizidine and Polyhydroxy Alkaloids Tropane Alkaloids Glycosides... 

Tropane alkaloids Tropane Atropine Cocaine Hyoscyamine Scopolamine/ hyoscine... 

L-ornithine Ornithine-derived alkaloids True alkaloids Pyrrolidine alkaloids Tropane alkaloids Pyrrolizidine alkaloids... 

Biologic Background Isoquinoline Alkaloids Terpenoid Indole Alkaloids Tropane Alkaloids Purine Alkaloids... 

PYRROLIDINE ALKALOIDS PYRROLIZIDINE ALKALOIDS TROPANE ALKALOIDS... 

Tropane alkaloids Tropane alkaloids Quinine Indole alkaloids Calystegins Glycoalkaloids... 

The wM-diacetate 363 can be transformed into either enantiomer of the 4-substituted 2-cyclohexen-l-ol 364 via the enzymatic hydrolysis. By changing the relative reactivity of the allylic leaving groups (acetate and the more reactive carbonate), either enantiomer of 4-substituted cyclohexenyl acetate is accessible by choice. Then the enantioselective synthesis of (7 )- and (S)-5-substituted 1,3-cyclohexadienes 365 and 367 can be achieved. The Pd(II)-cat-alyzed acetoxylactonization of the diene acids affords the lactones 366 and 368 of different stereochemistry[310]. The tropane alkaloid skeletons 370 and 371 have been constructed based on this chemoselective Pd-catalyzed reactions of 6-benzyloxy-l,3-cycloheptadiene (369)[311]. 

HjO), a picrate, m.p. 253° (dec.) and furnishes a dibenzoate, whose sulphate has [a] ° + 52-1° (EtOH) and hydrochloride, B. HCl. 2H2O, m.p. 115° or 205° (dry), + 41-8° (dilute alcohol) and nitrate, B. HNO3, m.p. 197°. On reduction with hydriodic acid and red phosphorus the dihydroxytropane is converted into tropane and on treatment with phosphorus oxychloride it yields a base, CgHjgON, b.p. 188°/752 mm., picrate, m.p. 177° (dec.). This dihydroxytropane is probably represented by formula (XIII).The dibenzoyl-derivative has local ansesthetic properties. The wovaleryl ester is the alkaloid valeroidine found in Duboisia myoporoides (p. 90). 

Of the other tropane alkaloids, convolvine (veratroylnortroplne), convolamme (veratroyltropine) and a number of their derivatives have been examined. All are stated to be local anaesthetics. ... 

Tritopine. See Laudanidine. Tropacocaine, 62, 64, 79, 100 pharmacological action, 106 Tropane, 87, 108 Tropane group alkaloids, 64, 776 pharmacological action, 105 Tropeines, 73, 79, 81 Tropehone, 80 Tropic acid, 72... 

Tropane Group. SolanaceOus Alkaloids, Convolvine and Allied Alkaloids, Dioscorine, Alkaloids of Coca Leaves (Erythroxylon coca). ... 

Biosynthesis of tropan alkaloids hyosciamine and scopolamine by isomerization of alkaloid littorine in Datura. stramonium and related species 98CSR207. 

A divergent synthesis of tropane alkaloid ferruginine was reported by Node and coworkers [59]. The P-ketoester intermediate was prepared by a novel PLE-catalyzed asymmetric dealkoxycarbonylation (hydrolysis followed by a decarboxylation) of a symmetric tropinone-type diester (Figure 6.12). Dimethyl sulfoxide was added to the phosphate buffer pH 8 (1 9) to reduce the activity of PLE and prevent over-deal-koxycarbonylation leading to tropinone. 

Aziridinocyclopropanes 163 derived from 2-phenylsulfonyl-l,3-dienes undergo BF3-induced rearrangement to bicyclic amines 165, which feature the skeleton of the tropane alkaloids. The reaction proceeds via cyclopropyl carbinyl cation 164, an intermediate also invoked in the analogous epoxide rearrangements. Trapping by fluoride ion is a competing pathway <96TL3371>. 

Heckrodt TJ, Mulzer J (2005) Marine Natural Products from Pseudopterogorgia Elisabe-thae Structures, Biosynthesis, Pharmacology and Total Synthesis. 244 1-41 Heinmaa I, see Samoson A (2005) 246 15-31 Helm L,see Toth E (2002) 221 61-101 Helmboldt H, see Hiersemann M (2005) 243 73-136 Hemscheidt T (2000) Tropane and Related Alkaloids. 209 175-206... 

Lawson, G., Ostah, N., and Woolley, J.G., MS/MS smdies of tropane alkaloids Detection and determination of stmctnre, m Applications of Modem Mass Spectrometry in Plant Science Research, Newton, R.P. and Walton, T.J., Eds., Clarendon Press, New York, 1996, chap. 16. 

From ornithine—tropane, pyrrolidine, pyrrolizide alkaloids, etc. 

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