Structure and Synthesis of Some Liverwort Metabolites

Salamani, Ahmid (1988) Structure and Synthesis of Some Liverwort Metabolites. MSc(R) thesis, University of Glasgow.

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Abstract

This thesis consists of four chapters. The first chapter, which is a General Introduction, deals with (i) the nature of secondary metabolites and (ii) the terpenoids and aromatic constituents of the liverworts. Chapter 2 describes several efforts to synthesise a lunularic acid derivative which occurs in the liverwort Plagiochila spinulosa. A Wittig reaction of 2-nitroveratraldehyde and 4-methoxybenzyl phosphonium chloride afforded a mixture of stilbenes which on reduction gave 2-amino-3,4,4'-trimethoxybibenzyl. This amino-bibenzyl was subjected to a Sandmeyer reaction in the hope of producing 2-cyano-3,4,4'-trimethoxybibenzyl. Unfortunately, the desired compound was obtained only in very low yield. The major product was 3,5,6-trimethoxy- 9,10-dihydrophenanthrene, the result of a Pschorr cyclisation. A similar Wittig route was used to prepare 2- bromo-3,4,4'-trimethoxybibenzyl. Attempts at carboxylation resulted only In debromination. Chapter 3 concerns a discussion of the constituents of Plagiochila spinulosa. Five dihydrophenanthrene derivatives were isolated together with methyl 2-methyl-3,4-methylene-dioxy-6-methoxybenzoate and an unusual natural product spinuloplagin B which is a diterpenoid-bibenzyl conjugate. A synthesis of 2-hydroxy-3,7-dimethoxy-9,10,-dihydrophen-anthrene is also described. The final chapter considers the metabolites of Frullania tamarisci. In addition to the known compounds (-) frullanolide and tamariscol, a new dimeric sesquiterpenoid lactone was isolated.

Item Type: Thesis (MSc(R))
Qualification Level: Masters
Keywords: Biochemistry
Date of Award: 1988
Depositing User: Enlighten Team
Unique ID: glathesis:1988-77814
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 14 Jan 2020 11:53
Last Modified: 14 Jan 2020 11:53
URI: http://theses.gla.ac.uk/id/eprint/77814

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