Wolff/Cope Approach to the AB Ring of the Sesterterpenoid Variecolin.

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.

SUBMITTER: Krout MR 

PROVIDER: S-EPMC6035096 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature