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Title: Synthesis of the aglycones of pseudopterosins
Author: Pontiroli, Alessandro
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 1997
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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 The route to pseudopterosins A-E started from (-)-citronellal and employed catalytic asymmetric reduction of , -unsaturated ester 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)
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry Chemistry, Organic