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Title: The synthesis of natural products by phenolic oxidation using hypervalent iodine reagents
Author: Satchwell, P. J.
Awarding Body: University of Wales Swansea
Current Institution: Swansea University
Date of Award: 1998
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Oxidation of a 2-(4"-hydroxybenzyl)-3-(3',4'dimethoxybenzyl) butyrolactone, using the hypervalent iodine reagents bis(trifluoroacetoxy) iodobenzene (PIFA) or iodobenzene diacetate (PIDA), results in the formation of 3-([1"-hydroxy-4"-oxo-2",5"cyclodienyl] methylene)-4-(3',4' dimethoxy benzyl)-2-(5H)-furanone in high yield. Treatment of 3-([1"-hydroxy-4"-oxo-2",5" cyclodienyl] methylene)-4-(3',4' dimethoxy benzyl)-2-(5H)-furanone with trifluoracetic acid results in rearrangement, to form 11-hydroxy-2-3 dimethoxy dibenzo[1a,4a:8a,12a] cycloocta-6-(hydroxymethyl)-7-(carboxylic acid) lactone, in quantitative yield. Hence we have achieved a highly efficient method to produce isostegane and stegane type lignans. Attempts to modify the oxidation of 2-(4"hydroxybenzyl)-3-(3',4'dimethoxybenzyl) butyrolactone, in order to produce the corresponding quinone methide, gave disappointing results. Oxidation of 2-(4"hydroxy 3",5" dimethoxybenzyl)-3-(3',4'dimethoxybenzyl) butyrolactone using silver complexes resulted in formation of 3',4'dimethoxybenzyl butrolactone. Oxidation of cis-3' hydroxy isoflavan-4-ol, to produce the corresponding pterocarpan, results in oxidation of both hydroxyls to produce a dimethoxy cyclohexadienone in acceptable yields.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available