Naturalproductman’s Blog

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Cubitane Synthesis

Posted by naturalproductman on January 19, 2010

Thomas Lindel and co-workers at TU Braunschweig have recently published in Organic Letters on the enantioselective synthesis of a cubitane carbon skeleton that is a 12-membered macrocycle.  The method they used was the radical cyclization approach.  There is a carbon carbon bond cleavage involved that requires the introduction of an alpha-hydroperoxy group on a ketone followed by an alkyl shift, which leads to the generation of an oxacarbenium ion that gets hydrolyzed to yield the 12-membered macrocycle.  The alpha-hydroperoxy ketone intermediate is generated by treating the ketone with lithium aluminum hydride in ether for 2 days under air exposure.

cubitane
OL paper

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