Synthesis of the Aglycones of Pseudopterosins

Pontiroli, Alessandro (1997) Synthesis of the Aglycones of Pseudopterosins. PhD thesis, University of Glasgow.

Abstract

The stereocontrolled and efficient syntheses of the aglycones of the potent anti-inflammatory pseudopterosins A-F and K-L have been achieved starting from convenient monoterpenic units and using a novel benzannulation protocol partially developed in or laboratories.

For the synthesis of the K-L compounds a completely substrate-controlled stereoselective route was devised starting from commercial isopulegol using a sequence of epoxidation and Lewis acid-promoted oxirane opening followed by benzannulation and Friedel-Crafts type sulphone displacement to generate the tricyclic structure of 3.2.1.13.

The route to pseudopterosins A-E started from (-)-citronellal and employed catalytic asymmetric reduction of , -unsaturated ester 8.2.1.5. After the formation of the aromatic ring, the second approach was convergent to the enantiomers of intermediates used in the first route. Oxidation with Fremy's salt led to the unstable aglycones of the natural compounds under mild conditions. (Fig. 3876A)

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Kocienski, Prof. Philip
• Date of Award: 1997
• Depositing User: Angi Shields
• Unique ID: glathesis:1997-4063
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 01 Mar 2013 12:53
• Last Modified: 01 Mar 2013 12:53
• URI: https://theses.gla.ac.uk/id/eprint/4063