872530-19-3Relevant academic research and scientific papers
A triple diene-transmissive Diels-Alder strategy to build the quassinoid framework
Dion, Amelie,Dube, Pascal,Spino, Claude
, p. 5601 - 5604 (2007/10/03)
(Chemical Equation Presented) An advanced intermediate to the highly oxygenated triterpene quassinoids was prepared in 14 steps from tetrahydrofuran. The key steps are three diene-transmissive Diels-Alder cycloadditions. Several features of this synthesis are noteworthy, including a successful Mitsunobu reaction on an allenylic alcohol, a rare [4 + 2] cycloaddition involving an enethiol ether dienophile, and complete control over all 10 chiral centers created.
