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Wolff/Cope Approach to the AB Ring of the Sesterterpenoid Variecolin
Michael R Krout1, Christopher E Henry2, Thomas Jensen3
1Department of Chemistry , Bucknell University , Lewisburg , Pennsylvania 17837 , United States.
Abstract:
A stereoselective synthesis of the AB ring of the complex sesterterpenoid variecolin is presented. Our strategy features the development of a tandem Wolff/Cope rearrangement of α-diazo cyclobutyl ketones for the construction of fused, 8-membered carbocycles. Preliminary studies revealed a facile Wolff rearrangement but a difficult vinyl ketene cyclobutane Cope rearrangement. We have leveraged an efficient microwave-promoted tandem rearrangement to prepare the desired functionalized cyclooctadienones that we envision as potential key intermediates in the convergent synthesis of variecolin.
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