TITLE

Part 1: Efficient strategies for the construction of variably substituted bicyclo[5.3.1]undecenones (AB taxane ring systems)

AUTHOR(S)
Laurent, Alain; Villalva-Servin, Nidia P.; Forgione, Pat; Wilson, Peter D.; Smil, David V.; Fallis, Alex G.
PUB. DATE
February 2004
SOURCE
Canadian Journal of Chemistry;Feb2004, Vol. 82 Issue 2, p215
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
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.
ACCESSION #
12556661

 

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