ArticleNature synthesis2025
The combination of synthesis and ultra-high-resolution NMR spectroscopy reveals the correct structure of caylobolide A.
Article in Nature synthesis, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Canalesolide A, a Structurally Unique Polyhydroxy Macrolide from the Marine Cyanobacterium Okeania sp. with Potent Antitrypanosomal Activity.Journal of the American Chemical Society · 2026Article
- Catalytic Scalable Synthesis of Polyketides Enabled by Chiral Brønsted Acid-Catalyzed Asymmetric Allylborations.Chemical record (New York, N.Y.) · 2026Review
- Caylobolide B: Structure Revision, Total Synthesis, Biological Characterization, and Discovery of New Analogues.Angewandte Chemie (International ed. in English) · 2026Article
- The combination of synthesis and ultra-high-resolution NMR spectroscopy reveals the correct structure of caylobolide A.Nature synthesis · 2025Article
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8 authors.
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Abstract
Polyketide-derived natural products bearing repeat 1,5-polyols are commonly encountered but their structures are notoriously difficult to determine using spectroscopic techniques. The presence of distal 1,5-diol moieties frequently leads to spectral overlap and chemical shift degeneracy, giving rise to ambiguity in their assignment. Caylobolide A is a representative member of this class of natural products, bearing a 36-membered lactone, with six 1,5-diol units and two 1,3-diol units. Its partial structure had been proposed, but only 4 of the 12 stereogenic centres had been assigned. Here we report a blueprint for the structure determination of this class of natural products, comprising the use of ultra-high-resolution NMR spectroscopy, Mosher's ester analysis and an efficient mixed isomer synthesis to unveil the correct structure of caylobolide A. With this approach, the partial stereochemistry proposed and the position of the triol unit within the carbon chain has been reassigned, culminating in the total synthesis of caylobolide A in 17 steps.
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