Organic Letters
Organic Letters
5 years ago

Chemical Transformations of the Fungal Meroterpenoid Dhilirolide A Reveal Skeletal Degradation and Rearrangement Reactions with Biosynthetic Implications

Chemical Transformations of the Fungal Meroterpenoid Dhilirolide A Reveal Skeletal Degradation and Rearrangement Reactions with Biosynthetic Implications
Raymond J. Andersen, E. Dilip de Silva, Ryan Centko, David E. Williams, Krista M. Wong
Treatment of the fungal meroterpenoid dhilirolide A (1) with either sodium azide or perchloric acid results in conversion of the dhilirane carbon skeleton of 1 to the 14,15-dinordhilirane carbon skeleton of the products 5–7, with and without concomitant transfer of an acetyl residue to form a C-9 acetate ester. The discovery of these transformations, which are vinylogous retro-Claisen-type condensations, suggests an efficient biogenetic route to 14,15-dinordhiliranes such as dhilirolide K (3).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02037

DOI: 10.1021/acs.orglett.7b02037

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