
%0 Journal Article
%A Banwell, Martin G. 
%A McLeod, Malcolm D. 
%A Riches, Andrew G. 
%T Taxane Diterpene Synthesis Studies. Part 2: Towards Taxinine&#8212;Enantiospecific Construction of an AB-ring Substructure Incorporating both Quaternary Carbon Centres and Attempts to Annulate the C-ring
%J Australian Journal of Chemistry
%D 2004/01/06
%V 57
%N 1
%P 53-66
%K anionic oxy-Cope rearrangement &#8212; cis-1,2-dihydrocatechols &#8212; Diels &#8212; Alder reactions &#8212; natural products &#8212; Taxinine
%R https://doi.org/10.1071/CH03161
%U https://www.publish.csiro.au/paper/CH03161 
%X 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&#8211;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 product enolate 25, bicyclo[5.3.1]undecenone 27 embodying the AB-ring system of target 1. Two methods for allylic oxidation of such products were developed and several unsuccessful attempts to effect a cyclization reaction so as to establish the taxane C-ring are described. 
