Work

Convergent Total Synthesis of Aleutianamine

Year: 2025

Type: article

Abstract: Herein, we describe a convergent total synthesis of the pyrroloiminoquinone natural product aleutianamine that exemplifies a novel paradigm for pyrroloiminoquinone synthesis by hinging upon a convergent intermolecular carbon-carbon bond forming event. Specifically, the coupling of a pyrroloquinone monoketal and a siloxythiophene fragment, each prepared in seven steps from commercially available materials, allows for access to the entire carbon framework of aleutianamine in only eight steps. A variety of intriguing skeletal rearrangements, minimal late-stage redox adjustments, and a carefully choreographed sequence of carbon-nitrogen bond formations then deliver the natural product.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.4c12946

Authors: Joseph P. Tuccinardi, John L. Wood

Institution: Baylor University

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500