- Probes for Narcotic Receptor Mediated Phenomena. 9. Synthesis of (+/-)-(3α,6aα,11aβ)-1,3,4,5,6,11a-Hexahydro-2-methyl-2H-3,6a-methanobenzofuroazocin-10-ol, an Oxide-Bridged 5-(m-Hydroxyphenyl)morphan
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The synthesis of racemic (3α,6aα,11aβ)-1,3,4,5,6,11a-hexahydro-2-methyl-2H-3,6a-methanobenzofuroazocin-10-ol (2d) is described.The route used acid-catalyzed ring closure of enamine 5 to yield the unsaturated phenylmorphan 6.Conversion of 6 to oxide
- Burke, Terrence R.,Jacobson, Arthur E.,Rice, Kenner C.,Weissman, Ben Avi,Huang, Hsueh-Cheng,Silverton, J. V.
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p. 748 - 751
(2007/10/02)
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- 4-Aryl-4-piperidinecarbinols
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4-Aryl-4-piperidinecarbinols, for example, STR1 useful as antidepressants and, in some cases, as anorectic agents.
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- Convenient Synthesis of 3-Methyl-2,3,4,4aα,5,6,7,7aα-octahydro-1H-benzofuroisoquinoline
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A new synthesis of 3-methyl-2,3,4,4aα,5,6,7,7aα-octahydro-1H-benzofuroisoquinoline (3) has been developed.The synthesis utilizes the acylation of anion 5 with γ-butyrolactone preferentially at the 4-position.Reduction of the resulting keto alcohol
- Shenvi, Ashok B.,Ciganek, Engelbert
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p. 2942 - 2947
(2007/10/02)
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- Certain tetrahydropyridine intermediates
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Process for preparing analgesic and narcotic antagonistic isoquinolines comprising: (a) contacting and reacting a lithiated anisole or alkyl phenyl ether, optionally substituted at the 3-position to the lithium atom, with a 4-piperidone to yield a 4-aryl-4-piperidinol; (b) dehydrating the piperidinol to a 4-aryl-1,2,3,6-tetrahydropyridine; (c) metalating and acylating the 1,2,3,6-tetrahydropyridine to yield a 1-(4-aryl-1,2,3,4-tetrahydropyrid-4-yl)-4-hydroxy-1-butanone; (d) reducing the ketone moiety of the butanone to yield a 5-aryl-7-oxa-2-azabicyclo[3.2.1]-octane-6-propanol; (e) converting the alcohol moiety of the propanol to L to yield a 5-aryl-6-[3-(L)propyl]-7-oxa-2-azabicyclo[3.2.1]octane in which L is a leaving group selected from the group consisting of -Cl, -Br, -I, p-MeC6 H4 SO3 - and MeSO3 -. (f) opening the amino furan ring of the bicyclooctane to yield a 4-(L)-1-(4-aryl-1,2,3,4-tetrahydropyrid-4-yl)-1-butanol derivative; (g) closing the 6-carbon ring of the butanol derivative by intramolecular reaction of the enamine and leaving group to yield a 4a-aryl-2,3,4,4a,5,6,7,8-octahydro-5-isoquinolinol or derivative thereof; and (h) reducing the enamine double bond of the octahydro-5-isoquinolinol or derivative thereof to yield a 4a-aryldecahydro-5-isoquinolinol or derivative thereof and (i) cyclizing the decahydro-5-isoquinolinol or derivative to yield a 2,3,4,4a,5,6,7,7a-octahydro-1H-benzofuro-[3,2-e]isoquinoline, or, (h) cyclizing the octahydro-5-isoquinolinol or derivative thereof to yield a 2,3,5,6,7,7a-hexahydro-1H-benzofuro-[3,2-e]isoquinoline and (i) reducing the enamine double bond of the isoquinoline.
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- STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF MORPHINE ALKALOIDS
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Application of metallated enamines to the synthesis of morphine related congeners is reported.A formal total synthesis of (+/-)-morphine has been completed.
- Evans, D. A.,Mitch, C. H.
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p. 285 - 288
(2007/10/02)
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