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DC Field | Value | Language |
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dc.contributor.advisor | MacLean, David | - |
dc.contributor.author | Jahangir | - |
dc.date.accessioned | 2019-02-26T20:16:10Z | - |
dc.date.available | 2019-02-26T20:16:10Z | - |
dc.date.issued | 1986-12 | - |
dc.identifier.uri | http://hdl.handle.net/11375/23950 | - |
dc.description.abstract | The usefulness of imines and iminium salts in the convergent synthesis of alkaloids and their synthetic analogues is described. Thus the anion derived from [3,4-c]pyridin-3[1H]-one, by treatment with LDA (lithium diisopropylamide) or LHS, (lithium bis-trimethylsilylamide) reacts with 2-methyl-3, 4-dihydro- isoquinolinium salts yielding aza analogues of phthalideisoquinoline alkaloids. The condensation of the same anion with 3,4-dihydroisoquinolines has provided, in a single step, azaprotoberberines containing the benzo[a)pyrido[3,4-g]quinolizine structure found in a number of Alangium alkaloids. The reaction of methyllithium with oxoberberine as a means of introducing a methyl group C-8 is described. The resulting iminium salt was reduced to a mixture of racemic a- and B-8-methylcanadines. This reaction has been applied to the synthesis of the Alangium alkaloid (+/-)-alamaridine. Condensation of lithium salts of 3-cyano-4-methylpyridine and 3-cyano-4-methyl-5-vinylpyridine with a complex of 3 ,4-dihydroisoquinolines and trimethylsilyl trifluoromethanesulphonate has been studied. The amidines formed as condensation products were transformed by hydrolysis into 5,6,13,14-tetrahydro-8H-isoquino[2,1-b][2,7]-naphthyridin-8-ones, a ring system found in several alkaloids of Alangtum lamarckii. These reactions have been employed in the synthesis of the Alangium alkaloids, (±)-alangimaridine and alangimarine. The usefulness of this reaction has been further demonstrated in the synthesis of N-benzyl derivatives of 3,14-dihydronauclefine and 3,14-dihydroangustine containing 8,13,13b,14-tetrahydroindolo[2•,3•:3,4]pyrido[1,2-b][2,7]-naphthyridin- 5[7H]-one. | en_US |
dc.language.iso | en | en_US |
dc.subject | imines | en_US |
dc.subject | iminium salts | en_US |
dc.subject | alkaloid synthesis | en_US |
dc.title | Use of Imines and Iminium Salts in Alkaloid Synthesis | en_US |
dc.type | Thesis | en_US |
dc.contributor.department | Chemistry | en_US |
dc.description.degreetype | Thesis | en_US |
dc.description.degree | Doctor of Philosophy (PhD) | en_US |
Appears in Collections: | Digitized Open Access Dissertations and Theses |
Files in This Item:
File | Description | Size | Format | |
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Jahangir_1986_12_phd.pdf | 34.94 MB | Adobe PDF | View/Open |
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