Part 1: Efficient strategies for the construction of variably substituted bicyclo[5.3.1]undecenones (AB taxane ring systems)
- 1 February 2004
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 82 (2) , 215-226
- https://doi.org/10.1139/v03-200
Abstract
Strategies for the construction of cyclic molecules containing variably substituted bicyclo[5.3.1]undecenones (AB taxane ring systems) are described. These routes employ a multi-component coupling protocol that utilizes sequential magnesium-mediated carbometallation of propargyl alcohols and intramolecular Diels–Alder reactions (IMDA). The cycloaddition generates the key eight-membered taxane ring as a single diastereomer, induced by preferential Lewis acid (diethylaluminum chloride or boron trifluoride etherate) complexation with the cross-ring oxygens. Both the electronic nature of the dienophile and the neighbouring group non-bonded interactions contribute to the success of these cycloadditions.Key words: magnesium chelate, Lewis acid, intramolecular Diels–Alder, cycloaddition.Keywords
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