ArticleJournal of the American Chemical Society2024
Total Synthesis of the Allenic Macrolide (+)-Archangiumide.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Gold catalysis toward the synthesis of natural products: a review.RSC advances · 2026Review
- Square-Planar Ruthenium Alkylidyne Complexes Undergo Stepwise Rather Than Concerted [2 + 2] Cycloadditions with Alkynes.Angewandte Chemie (International ed. in English) · 2026Article
- Collective Total Synthesis of a Unique Class of Liverworts-Derived Cembrane Diterpenoids.Angewandte Chemie (International ed. in English) · 2025Article
- Early Intervention in Herpes Simplex Virus-1 Replication in Vitro with Allenic Macrolide Archangiumide.International journal of molecular sciences · 2025Article
- Molybdenum(VI) Nitrido Complexes with Tripodal Silanolate Ligands. Structure and Electronic Character of an Unsymmetrical Dimolybdenum μ-Nitrido Complex Formed by Incomplete Nitrogen Atom Transfer.Inorganic chemistry · 2024Article
Corrections and comments
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Authors and funding
2 authors.
Funding
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Abstract
Archangiumide is the first known macrolide natural product comprising an endocyclic allene. For the ring strain that this linear substructure might entail, it was planned to unveil the allene at a very late stage of the projected total synthesis; in actual fact, this was achieved as the last step of the longest linear sequence by using an otherwise globally deprotected substrate. This unconventional timing was made possible by a gold catalyzed rearrangement of a macrocyclic propargyl benzyl ether derivative that uses a -PMB group as latent hydride source to unveil the signature cycloallene; the protecting group therefore gains a strategic role beyond its mere safeguarding function. Although the gold catalyzed reaction per se is stereoablative, the macrocyclic frame of the target was found to impose high selectivity and a stereoconvergent character on the transformation. The required substrate was formed by ring closing alkyne metathesis (RCAM) with the aid of a new air-stable molybdenum alkylidyne catalyst.
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Registered trials
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