Work

A Divergent Asymmetric Total Synthesis of Coprophilin and Four Trichodermic Acids via a [1,5]-Hydride Shift–Aldol Cascade

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide The asymmetric syntheses of coprophilin and four members of the trichodermic acid family of natural products are disclosed. Our work employs a number of key transformations, including an aluminum-promoted [1,5]-hydride shift–aldol cascade reaction, an exo -selective Diels–Alder cycloaddition, and a late-stage Fleming–Tamao oxidation. These key steps efficiently construct the bicyclic core of the natural products, which can then be readily functionalized in a divergent manner, allowing the synthesis of a wide range of natural product targets.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5c17359

Authors: Edward Smith, Timothy C. Jenkins, Charles S. Yeung, Timothy J. Donohoe

Institutions: University of Oxford, Merck & Co., Inc., Rahway, NJ, USA (United States)

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500