Skip to content Skip to navigation
University of Warwick
  • Study
  • |
  • Research
  • |
  • Business
  • |
  • Alumni
  • |
  • News
  • |
  • About

University of Warwick
Publications service & WRAP

Highlight your research

  • WRAP
    • Home
    • Search WRAP
    • Browse by Warwick Author
    • Browse WRAP by Year
    • Browse WRAP by Subject
    • Browse WRAP by Department
    • Browse WRAP by Funder
    • Browse Theses by Department
  • Publications Service
    • Home
    • Search Publications Service
    • Browse by Warwick Author
    • Browse Publications service by Year
    • Browse Publications service by Subject
    • Browse Publications service by Department
    • Browse Publications service by Funder
  • Help & Advice
University of Warwick

The Library

  • Login
  • Admin

Some chemistry relating to turmerones

Tools
- Tools
+ Tools

Pombo-Villar, Esteban (1985) Some chemistry relating to turmerones. PhD thesis, University of Warwick.

[img]
Preview
PDF
WRAP_Theses_Pombo-Villar_1985.pdf - Unspecified Version - Requires a PDF viewer.

Download (8Mb) | Preview
Official URL: http://webcat.warwick.ac.uk/record=b1445493~S15

Request Changes to record.

Abstract

The current ideas relating to the biosynthesis of turmerones are discussed, and a biosynthetic pathway leading to α- and β-turmerones is proposed. The conformation of β-turmerone assigned by Japanese workers is shown to be based on erroneous assumptions; their data are insufficient for assignment of the absolute stereochemistry of β-turmerone. A chemical correlation to juvabione is proposed, and all current methodology is inadequate for the selective transformation of a 1, 3-diene to an α β-unsaturated methyl ester. It is shown that this transformation can be performed via the addition of a sulphenyl halide to the 1, 3-diene. Addition of phenylsulphenyl chloride to 2, 3-dimethyl-l, 3-butadiene gives the 1, 2-adduct: 2-chloro-2, 3-dimethyl-l-(phenylthio) but-3-ene. This adduct rearranges thermally to the 1, 4-adduct. The 1, 2-adduct is converted into a variety of β-substituted sulphides by replacing the chloride with a suitable nucleophile: MeOˉ , AcOˉ , ˉCN, ˉOH. Hydride transfer to the tertiary centre is slow, and rearrangement to the 1, 4-adduct is a competing process. Conversion of β-hydroxy- sulphides from 1, 3-dienes to alkenylepoxides is achieved, and the epoxides rearrange to aldehydes by acid treatment. This constitutes an oxidative monofunctionalisation of 1, 3-dienes, and similar transformations are obtained with 4,4-dimethyl-l-methylenecyclohex-2-ene, and with trans-penta-1,3-diene. The thermolysis of (2-hydroxy-l-phenyl- ethyl)pyridinecobaloxime is studied by 1 HNMR, and employed to synthesise l-(carboxymethyl)ethylpyridinecobaloxime. No alkylcobalt species is obtained in the reaction with dienes or unactivated olefins.

Finally, the determination of the structure of a new lignan from Virola elongata is described.

Item Type: Thesis (PhD)
Subjects: Q Science > QK Botany
S Agriculture > SB Plant culture
Library of Congress Subject Headings (LCSH): Plant products -- Synthesis , Turmeric -- Analysis, Virola (Genus)
Official Date: September 1985
Dates:
DateEvent
September 1985Submitted
Institution: University of Warwick
Theses Department: Department of Chemistry and Molecular Sciences
Thesis Type: PhD
Publication Status: Unpublished
Supervisor(s)/Advisor: Golding, Bernard T. ; Samuel, Christopher J.
Sponsors: Icetex ; Quest International ; Overseas Research Scholarship ; COBE. S. A. ; Imperial Chemical Industries, ltd. ; Procter & Gamble Company
Extent: 1 volume (various pagings) : illustrations
Language: eng

Request changes or add full text files to a record

Repository staff actions (login required)

View Item View Item

Downloads

Downloads per month over past year

View more statistics

twitter

Email us: wrap@warwick.ac.uk
Contact Details
About Us