Tropan

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]. 

If, iastead of an acetoacetate equivalent, a malonyl derivative such as (39) were iavolved (37), appropriate condensation reactions would lead to the tropane [280-05-7] skeleton (40),... 

Valeroidine C13H33O3N Dihydroxy- tropane iSoValerie acid... 

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. ... 

Not only may tropane be extended externally, as in homotropme (. but a new methylene group may be inserted in the heptamethylene rinj thus Werner has shown that -pclleticrine (VII), on reduction in differe ways, yields two granatolines (VIII), corresponding, no doubt, to tropi... 

The first complete formula (I) suggested for lupanine was that of Thoms and Bergerhoff, based mainly on the formation of 2-ethylpyridine when lupanine was distilled with zinc dust, which seemed to indicate a similarity between tropane and lupanine. 

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). ... 

Teloidine, the basic hydrolytic product of meteloidine, has been synthesised recently under physiological conditions by Schdpf and Arnold, on the lines of the tropinone synthesis, mesotartaric aldehyde (CHOH. CHO)j, being condensed at 25° with aeetonediearboxylic acid bnd methylamine hydrochloride to teloidinone (5-keto-l 2-dihydroxy-tropane) whieh on eatalytic hydrogenation yielded teloidine (1 2 5-trihydroxytropane). 

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

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