Studies in the Lignan and Terpene Fields

Gilchrist, Thomas (1962) Studies in the Lignan and Terpene Fields. PhD thesis, University of Glasgow.

Abstract

Lignan Section. Otoba fat has been shown to contain a hydroxy otobain and a mixture of phenols in addition to otobain. A structure is proposed for otobain, on the basis of its degradation products and its nuclear magnetic resonance spectrum. The 1-phenylnaphthalenes, 7,8 : 7 1,8 1-tetradehydropipero- cyclolignan and 3,4 : 2 1 ,3 1-bis-methylenedioxy-7,8 : 7 1, 8 1-tetradehydro-cyclolignan, which are related to tetradehydro-otobain, have been synthesised from piperonal type precursors. Attempted syntheses of tetradehydro-otobain are also reported. Terpene Section Synthetic routes to aromatic diterpenoids have been investigated which involved suitably substituted phenylcyclohexanones as precursors. 2,6,6-Trimethyl-2-phenylcyclohex-3-enone was prepared from o-hydroxydiphenyl but proved resistant to external attack on its carbonyl function. Several routes to this compound possessing a side chain suitably substituted for internal attack on the hindered ketone were also investigated.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1962
• Depositing User: Enlighten Team
• Unique ID: glathesis:1962-79457
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 05 Mar 2020 09:31
• Last Modified: 05 Mar 2020 09:31
• URI: https://theses.gla.ac.uk/id/eprint/79457