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.

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: https://theses.gla.ac.uk/id/eprint/80184