ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. 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.
- Ring opening of epoxides: a facile approach towards the synthesis of polyketides and related stereoenriched natural products: a review.Molecular diversity · 2025Review
- Genetic engineering of Sorangium cellulosum reveals hidden enzymology in myxobacterial natural product biosynthesis.Nature communications · 2025Article
- Combining total synthesis and genetic engineering to probe dihydropyran formation in ambruticin biosynthesis.Chemical science · 2024Article
- The Corey-Seebach Reagent in the 21st Century: A Review.Molecules (Basel, Switzerland) · 2023Review
- Synthetic and biosynthetic methods for selective cyclisations of 4,5-epoxy alcohols to tetrahydropyrans.Organic & biomolecular chemistry · 2022Review
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4 authors.
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Abstract
The family of anti-fungal natural products known as the ambruticins are structurally distinguished by a pair of pyran rings adorning a divinylcyclopropane core. Previous characterization of their biosynthesis, including the expression of a genetically modified producing organism, revealed that the polyketide synthase pathway proceeds via a diol intermediate, known as ambruticin J. Herein, we report the first enantioselective total synthesis of the putative PKS product, ambruticin J, according to a triply convergent synthetic route featuring a Suzuki-Miyaura cross-coupling and a Julia-Kocienski olefination for fragment assembly. This synthesis takes advantage of synthetic methodology previously developed by our laboratory for the stereoselective generation of the trisubstituted cyclopropyl linchpin.
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