
TY  - JOUR
A1  - Banwell, Martin G. 
A1  - McLeod, Malcolm D. 
A1  - Riches, Andrew G. 
T1  - 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
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2004
VL  - 57
IS  - 1
SP  - 53
EP  - 66
KW  - anionic oxy-Cope rearrangement &#8212; cis-1,2-dihydrocatechols &#8212; Diels &#8212; Alder reactions &#8212; natural products &#8212; Taxinine
UR  - https://doi.org/10.1071/CH03161 
N2  - 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. 
ER  -

