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

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.

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Publication Details

Journal
Organic Letters
Published
2026-03-24
DOI
https://doi.org/10.1021/acs.orglett.6c00438
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
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article

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

Organic Letters
Cyclopropane Reaction Mechanisms
article

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

article en

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.

Organic Letters
University of California, Davis (US)
Openalex Percentile: Top 11%
Cyclopropane Reaction Mechanisms
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Remote Stereocontrol in Aryl/Alkyl C–H Insertion Reactions of Rhodium Carbenes: Assembly of Pseudorigidols A and B · Organic Letters (2026) | TGRS Research Map | TGRS