Journal of Organic Chemistry p. 6995 - 7009 (2018)
Update date:2022-08-17
Topics:
Krout, Michael R.
Henry, Christopher E.
Jensen, Thomas
Wu, Kun-Liang
Virgil, Scott C.
Stoltz, Brian M.
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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