Synthesis of taxoid analogues via tether controlled cycloaddition reactions.

Jodi Anne. Lavers
The syntheses of potential Taxol$\sp\circler$ analogues 35 and 57-b are described. The route selected employed a planar group (aromatic ring or a double bond) in the tether to facilitate the key step, an intramolecular Diels-Alder reaction. This approach afforded the tricyclic core of 35 in an efficient and direct manner. The Diels-Alder precursor 33 was synthesized from 3-methylbenzyl alcohol, acrolein, and (Z)-1-iodo-2-p-methoxybenzyloxymethyl-1,3-butadiene (15). The cyclization of alcohol 33 proceeded readily under oxidative conditions at room...
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