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DOI: 10.1055/a-1659-6521
Diastereoselective Synthesis of the ABCD Ring System of Rubriflordilactone B
This project was supported by NSF-CAREER award CHE-1352490.


Abstract
A novel nine-step diastereoselective route to the ABCD ring system of the natural product rubriflordilactone B is reported. Use of an α-substituted butenolide derived from maleic anhydride facilitated a 1,4-conjugate addition to provide a diene. The order in which a ring-closing metathesis and enolate oxidation were performed on this compound dictated the relative stereochemistry of the target. The final product exhibited anisotropic effects during room-temperature NMR studies, requiring elevated-temperature experiments to confirm its identity.
Key words
rubriflordilactone B - synthesis - diastereoselectivity - butanolides - variable-temperature NMR - ring-closing metathesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1659-6521.
- Supporting Information
- CIF File
Publikationsverlauf
Eingereicht: 10. September 2021
Angenommen nach Revision: 01. Oktober 2021
Accepted Manuscript online:
01. Oktober 2021
Artikel online veröffentlicht:
22. Oktober 2021
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