Studies in the Diterpenoid Field

Balmain, Allan (1969) Studies in the Diterpenoid Field. PhD thesis, University of Glasgow.

Abstract

The constitution and stereochemistry of epsilon-caesalpin, a furanoid diterpenoid from Caesalpinia bonducella, has been derived from chemical and spectroscopic evidence. The proposed structure was verified by x-ray analysis of a p-bromobenzoate derivative, which in addition provided the absolute configuration. An attempt to determine the absolute configuration of alpha-, beta- and delta-caesalpins by direct correlation with epsilon-caesalpin was unsuccessful. This research revealed several inconsistencies in the results of previous workers on the stereochemistry of these compounds, and evidence is presented which defines unambiguously the stereochemistry of the ring B substituents of alpha- (and hence beta- and delta-) caesalpin. The structures of six of the minor constituents of Caesalpinia bonducella are discussed. Extraction of the whole plant Andrographis paniculata afforded, in addition the known compounds andrographolide and neoandrographolide, three diterpenoid lactones which had not been previously isolated. The structures of these have been deduced from chemical and spectral data. The mass spectra of some andrographolide derivatives are discussed.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1969
• Depositing User: Enlighten Team
• Unique ID: glathesis:1969-78509
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 28 Feb 2020 12:09
• Last Modified: 28 Feb 2020 12:09
• URI: https://theses.gla.ac.uk/id/eprint/78509