Work

Remote Stereocontrol in Aryl/Alkyl C–H Insertion Reactions of Rhodium Carbenes: Assembly of Pseudorigidols A and B

Year: 2026

Type: article

Abstract: The first total syntheses of pseudorigidols A and B are reported. Our syntheses employ a rhodium-catalyzed C-H insertion reaction to build the tricyclic core. The catalyst screen revealed the influence of a remote stereogenic center on the diastereoselectivity of the insertion. Using two different catalysts, we were able to synthesize the two natural products with high diastereoselectivity. These results will lay the foundation for further studies on the influence of remote stereogenic centers.

Source: Organic Letters

DOI: 10.1021/acs.orglett.6c00438

Authors: Linda Ung, Sarah N. Dishman, Sophia Zhang, James C. Fettinger, Jared T. Shaw

Institution: University of California, Davis

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences

Awards: Purchase of an X-ray Diffractometer, G567070376, G6962853074