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Phenolic Oxidations of Totarol

Authors: RC Cambie; PI Higgs; CM Read; PS Rutledge; GR Ryan; PD Woodgate;

Phenolic Oxidations of Totarol

Abstract

Methods for the direct oxidation of the C12 position of totarol (1) or its methyl ether (4) have been examined. Treatment of (1) with benzeneseleninic anhydride gave the 9-hydroxy dienone (16) which on ozonolysis afforded the spiro butenolide (21), formed via the ozonide (22). The rearranged ether (18) was obtained from one oxidation with benzeneseleninic anhydride. Mercuriation of totarol and totaryl methyl ether gave the mercuriochlorides (5) and (7) but attempts to form the methoxy acetate (6) from (7) by boronation /oxidation and acetylation were unsuccessful. Treatment of totaryl methyl ether (4) with thallium(III) trifluoroacetate gave dienone 14- and 9-trifluoroacetates (25) and (17). Reaction of the (?6-arene) tricarbonylchromium(0) complexes (28) and (29) of (4) with lithioacetonitrile gave the 7a-alcohol (30) but reaction with t- butyllithium and then with copper(I) bromide/ dimethyl sulfide and MoOPH gave the methoxyphenol (12) in 66% yield.

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
7
Average
Top 10%
Average
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