5,6-dihydro-2<i>H</i>-pyran-2-ones are a family of enantioenriched natural products with varying acylation at C3, and with varying-length C6 carbon chains. An array of biological activities have been associated with such pyranones. Rhytismatones A and B were isolated in 2017 as anti-fungal compounds with an 8-carbon acyl group and unique acid and carbomethoxy substituents, respectively, at C6. The chirality of C6 has been assigned based on similarity to other compounds. This synthesis will confirm the absolute configuration and give access to the class of oxidized derivatives represented by rhytismatones A and B. The synthesis takes advantage of the enantioselective Mukaiyama aldol reaction to set the chiral center. This presentation will include our work to date, assembling a protected skeleton for rhytismatones A and B, and outlines future work to reveal the carboxylate, while avoiding possible complications due to racemization and deacylation.

Progress toward the enantioselective synthesis of rhytismatones A and B

Where thousands of chemistry professionals meet to share ideas and advance scientific and technical knowledge. Spring 2023 abstracts, posters, and presentations will launch at the end of March.

ACS Spring 2023

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.