ArticleAngewandte Chemie (International ed. in English)2021
The Formosalides: Structure Determination by Total Synthesis.
Article in Angewandte Chemie (International ed. in English), 2021. 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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- Total Synthesis of Benthol A: Evidence for a Structure Revision.Journal of the American Chemical Society · 2026Article
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- Stereoselective Syntheses of Cyclic Microsclerodermin Derivatives.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Tripodal Silanolate Ligands Expand [MoXJournal of the American Chemical Society · 2025Article
- Total Synthesis of the Norcembranoid Scabrolide B and Its Transformation into Sinuscalide C, Ineleganolide, and Horiolide.Journal of the American Chemical Society · 2024Article
- Rhenium Alkyne Catalysis: Sterics Control the Reactivity.Inorganic chemistry · 2024Article
- Second-Generation Total Synthesis of Prorocentin.Organic letters · 2023Article
- Total Syntheses of Nominal and Actual Prorocentin.Journal of the American Chemical Society · 2023Article
- Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- The Tetrahydrofuran Motif in Polyketide Marine Drugs.Marine drugs · 2022Review
- Total Syntheses of Scabrolide A and Nominal Scabrolide B.Journal of the American Chemical Society · 2022Article
- Regioselective trans-Hydrostannation of Boron-Capped Alkynes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- The Ascent of Alkyne Metathesis to Strategy-Level Status.Journal of the American Chemical Society · 2021Article
- A Unified Approach to Polycyclic Alkaloids of the Ingenamine Estate: Total Syntheses of Keramaphidin B, Ingenamine, and Nominal Njaoamine I.Journal of the American Chemical Society · 2021Article
- An Alkyne-Metathesis-Based Approach to the Synthesis of the Anti-Malarial Macrodiolide Samroiyotmycin A.Angewandte Chemie (International ed. in English) · 2021Article
- Total Synthesis of Leiodermatolide A via Transfer Hydrogenative Allylation, Crotylation, and Propargylation: Polyketide Construction beyond Discrete Allyl- or Allenylmetal Reagents.Journal of the American Chemical Society · 2021Article
- From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.ACS catalysis · 2021Article
- Scalable De Novo Synthesis of Aldgarose and Total Synthesis of Aldgamycin N.Angewandte Chemie (International ed. in English) · 2021Article
- Total Synthesis of Mycinolide IV and Path-Scouting for Aldgamycin N.Angewandte Chemie (International ed. in English) · 2021Article
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6 authors.
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Abstract
Total synthesis allowed the constitution of the cytotoxic marine macrolides of the formosalide family to be confirmed and their previously unknown stereostructure to be assigned with confidence. The underlying blueprint was inherently modular to ensure that each conceivable isomer could be reached. This flexibility derived from the use of strictly catalyst controlled transformations to set the stereocenters, except for the anomeric position, which is under thermodynamic control; as an extra safety measure, all stereogenic centers were set prior to ring closure to preclude any interference of the conformation adopted by the macrolactone rings of the different diastereomers. Late-stage macrocyclization by ring-closing alkyne metathesis was followed by a platinum-catalyzed transannular 6-exo-dig hydroalkoxylation/ketalization to craft the polycyclic frame. The side chain featuring a very labile unsaturation pattern was finally attached to the core by Stille coupling.
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