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Taxane Diterpene Synthesis Studies. Part 2: Towards Taxinine-Enantiospecific Construction of an AB-ring Substructure Incorporating both Quaternary Carbon Centres and Attempts to Annulate the C-ring

Banwell, Martin; McLeod, Malcolm; Riches, Andrew G


In connection with efforts to develop an efficient total synthesis of the biologically active natural product taxinine 1, the enzymatically-derived and monochiral cis-1,2-dihydrocatechol 7 was converted, over several steps including a Diels-Alder cycloaddition reaction, into the bicyclo[2.2.2]octan-2-one 18. Reaction of the last compound with the organocerium reagent 22 afforded the 1,5-diene 23 which engaged in an anionic oxy-Cope rearrangement reaction to give, after C-methylation of the...[Show more]

CollectionsANU Research Publications
Date published: 2004
Type: Journal article
Source: Australian Journal of Chemistry
DOI: 10.1071/CH03161


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