The Constitution and the Synthesis of the Alkaloid Anonaine

Weitnauer, Gustav Adolf (1939) The Constitution and the Synthesis of the Alkaloid Anonaine. PhD thesis, University of Glasgow.

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Abstract

The constitution of the alkaloid anonaine has been investigated. The following structural formula was suggested: It is based chiefly on the following experimental results: 1. Empirical formula for anonaine C17H15O2N. 2. Proof a methylenedioxy and a secondary amino-group. 3. Negative tests for methoxy, carbonyl, phenolic and alcoholic hydroxy groups. 4. The details of the Hofmann degradation as well as the effect of chloroethylcarbonate upon N. methyl-anonaine proved the isoquinoline structure of anonaine. 5. The formation of phthalic acid in the oxydation of anonaine proved that anonaine does not possess a papaverine structure. It showed further, that ring C is unsubstituted. By analogy the methylenedioxy group was assumed to be in position 5,6. The correctness of the suggested formula was proved by the synthesis of the alkaloid. d,1-anonaine and also d,1-N-methyl-anonaine were synthesised. These synthetic alkaloids were deprived of their asymmetric centres by a Hofmann degradationand the products thus obtained were proved to be identical with the corresponding degradation compounds of natural anonaine.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Organic chemistry
Date of Award: 1939
Depositing User: Enlighten Team
Unique ID: glathesis:1939-80184
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 02 Mar 2020 22:41
Last Modified: 02 Mar 2020 22:41
URI: http://theses.gla.ac.uk/id/eprint/80184

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