An Enantioselective Approach to (–)-Psiguadial A

22 October 2024, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

psiguadial A
meroterpenoids
ortho-quinone methide
cyclization

Supplementary materials

Title
Description
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Experimental details and spectral data
Description
Experimental procedures, NMR spectra, and crystallographic data.
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NMR Data
Description
Archive of NMR FID files for all compounds
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