ArticleJournal of the American Chemical Society2016
Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
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- Corey-Fuchs reaction enabled synthesis of natural products: a review.RSC advances · 2025Review
- Iminium Catalysis in Natural Diels-Alderase.Nature catalysis · 2025Article
- Ten-Step Total Synthesis of (±)-Phaeocaulisin A Enabled by Cyclopropanol Ring-Opening Carbonylation.Journal of the American Chemical Society · 2024Article
- CO-Free Aminocarbonylation of Terminal Alkynes Catalyzed by Synergistic Effect From Metal-Organic Frameworks.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Convergent and Efficient Total Synthesis of (+)-Heilonine Enabled by C-H Functionalizations.Journal of the American Chemical Society · 2024Article
- Recent Advances in Chemical Synthesis of Amino Sugars.Molecules (Basel, Switzerland) · 2023Review
- Heck Macrocyclization in Forging Non-Natural Large Rings including Macrocyclic Drugs.International journal of molecular sciences · 2023Review
- Palladium-Catalyzed Carbonylations: Application in Complex Natural Product Total Synthesis and Recent Developments.The Journal of organic chemistry · 2023Review
- Concise Synthesis of (-)-GAJournal of the American Chemical Society · 2023Article
- An SCCS chemistry · 2022Article
- General Method for the Synthesis of α- or β-Deoxyaminoglycosides Bearing Basic Nitrogen.Journal of the American Chemical Society · 2021Article
- Calcium Glycerolate Catalyst Derived from Eggshell Waste for Cyclopentadecanolide Synthesis.Frontiers in chemistry · 2021Article
- Modular Approaches to Lankacidin Antibiotics.Journal of the American Chemical Society · 2020Article
- Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes.Nature communications · 2020Article
- Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes.Molecules (Basel, Switzerland) · 2019Review
- Total Synthesis of trans-Resorcylide via Macrocyclic Stille Carbonylation.The Journal of antibiotics · 2019Article
- Total Synthesis, Biological Evaluation, and Target Identification of Rare Abies Sesquiterpenoids.Journal of the American Chemical Society · 2018Article
- Synthesis, Structural Reassignment, and Antibacterial Evaluation of 2,18-Seco-Lankacidinol B.Angewandte Chemie (International ed. in English) · 2018Article
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4 authors.
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Abstract
Spinosyn A (1), a complex natural product featuring a unique 5,6,5,12-fused tetracyclic core structure, is the major component of spinosad, an organic insecticide and an FDA-approved agent used worldwide. Herein, we report an efficient total synthesis of (-)-spinosyn A with 15 steps in the longest linear sequence and 23 steps total from readily available compounds 14 and 23. The synthetic approach features several important catalytic transformations including a chiral amine-catalyzed intramolecular Diels-Alder reaction to afford 22 in excellent diastereoselectivity, a one-step gold-catalyzed propargylic acetate rearrangement to convert 28 to α-iodoenone 31, an unprecedented palladium-catalyzed carbonylative Heck macrolactonization to form the 5,12-fused macrolactone in one step, and a gold-catalyzed Yu glycosylation to install the challenging β-forosamine. This total synthesis is highly convergent and modular, thus offering opportunities to synthesize spinosyn analogues in order to address the emerging cross-resistance problems.
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