Synthesis of two conformationally constrained analogues of the minor tobacco alkaloid anabasine.
The anabasine analogues spiro[4-azaindan-1,2'-piperidine] (7) and spiro[6-azaindan-1,2'-piperidine] (8) have been prepared. A series of palladium-catalyzed reactions, where an intramolecular cyclization constituted a key reaction, were utilized for the preparation of the two target compounds.
Lindström
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S
Department of Organic Pharmaceutical Chemistry, BMC, Uppsala University, Box 574, SE-751 23 Uppsala, Sweden.
Ripa
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Hallberg
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A
D000215:Acylation; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D000691:Anabasine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D003500:Cyclization; D009538:Nicotine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D010165:Palladium / Q000378:metabolism; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D010947:Plants, Toxic; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism; D014026:Nicotiana / Q000737:chemistry*
D000470:Alkaloids; D010880:Piperidines; D013141:Spiro Compounds; C413769:spiro(4-azaindan-1,2'-piperidine); C413782:spiro(6-azaindan-1,2'-piperidine); D010165:Palladium; D009538:Nicotine; D000691:Anabasine