Journal article

A divergent asymmetric total synthesis of coprophilin and four trichodermic acids via a [1,5]-hydride shift–aldol cascade

Abstract:: 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.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Smith, E., Jenkins, T. C., Yeung, C. S., & Donohoe, T. J. (2025). A divergent asymmetric total synthesis of coprophilin and four trichodermic acids via a [1,5]-hydride shift–aldol cascade. Journal of the American Chemical Society, 148(1), 1252–1258.

MLA Style

Smith, E, et al. “A Divergent Asymmetric Total Synthesis of Coprophilin and Four Trichodermic Acids via a [1,5]-Hydride Shift–Aldol Cascade.” Journal of the American Chemical Society, vol. 148, no. 1, 2025, pp. 1252–58.

Chicago Style

Smith, E, TC Jenkins, CS Yeung, and TJ Donohoe. 2025. “A Divergent Asymmetric Total Synthesis of Coprophilin and Four Trichodermic Acids via a [1,5]-Hydride Shift–Aldol Cascade.” Journal of the American Chemical Society 148 (1): 1252–58.
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Files:: Smith_et_al_2025_A_divergent_asymmetric_SI.pdf

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Publisher copy:: 10.1021/jacs.5c17359

Authors

+ Smith, E More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Chemistry Research Laboratory
Role:: Author

+ Jenkins, TC More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Chemistry Research Laboratory
Role:: Author

+ Yeung, CS More by this author

Role:: Author

+ Donohoe, TJ More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Chemistry Research Laboratory
Role:: Author

Publisher:: American Chemical Society
Journal:: Journal of the American Chemical Society More from this journal
Volume:: 148
Issue:: 1
Pages:: 1252-1258
Publication date:: 2025-12-18
Acceptance date:: 2025-12-04
DOI:: 10.1021/jacs.5c17359
EISSN:: 1520-5126
ISSN:: 0002-7863

Language:: English
Keywords:: aldol reactions

chemical synthesis

ketones

molecular structure

pharmaceuticals
Pubs id:: 2345549
Local pid:: pubs:2345549
Deposit date:: 2025-12-05
ARK identifier:: ark:/29072/ora_38a815dcb4ff4f6c971cd16aad72b2aa

Terms of use

Copyright holder:: Smith et al.
Copyright date:: 2025
Rights statement:: © 2025 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0 .

Licence:: CC Attribution (CC BY)

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