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An Enantioselective Approach to (–)-Psiguadial A

Year: 2024

Type: preprint

Abstract: The first enantioselective approach to the antiproliferative natural product (–)-psiguadial A is reported. This approach features the enantioselective synthesis of a complex tricyclic terpenoid precursor, the union of that precursor with a polyketide component by an enolate-ortho-quinone methide coupling reaction to form a highly congested carbon–carbon bond, and an acid mediated intramolecular hydration ring-closure leveraging a fully substituted alkene to generate the unique oxepane core structure of the natural product.

Source: ChemRxiv

DOI: 10.26434/chemrxiv-2024-ghb91-v2

Authors: Liam O'Grady, Marcel Achtenhagen, Michael Wisthoff, Robert Lewis, Katarina Pfeifer, Weifeng Zheng, Maxwell Martin, Glenn Yap, William Chain

Institutions: University of Delaware, Atea Pharmaceuticals (United States), Harvard University, Houston Methodist

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Cancer Institute

Award: Carbonyls to Cancer Therapeutics

OpenAlex ID: W4403658097

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