ArticleJournal of the American Chemical Society2022
Stereocontrolled Total Synthesis of Bastimolide B Using Iterative Homologation of Boronic Esters.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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18 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
- Selective Copper-Catalyzed Cross-Coupling of Cyclopropyl and Cyclobutyl 1,2-Bis(boronates).Organic letters · 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 Development of Stereoselective Substrate and Reagent-Controlled Lithiation-Borylation Chemistry.The Journal of organic chemistry · 2025Article
- 1,1-polymerization of acetylene.Nature communications · 2025Article
- One-carbon homologation of alkenes.Nature · 2025Article
- Syntheses of Marine Natural Products via Matteson Homologations and Related Processes.Marine drugs · 2025Review
- Cyclization by Intramolecular Suzuki-Miyaura Cross-Coupling-A Review.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- The combination of synthesis and ultra-high-resolution NMR spectroscopy reveals the correct structure of caylobolide A.Nature synthesis · 2025Article
- Marine Cyanobacteria: A Rich Source of Structurally Unique Anti-Infectives for Drug Development.Molecules (Basel, Switzerland) · 2024Review
- The current utility and future potential of multiborylated alkanes.Nature reviews. Chemistry · 2024Review
- A Three-Step Catalytic Asymmetric Sequence from Alkynes to α-Silyloxyaldehydes and Its Application to a C22-C41 Fragment of Bastimolide A.Organic letters · 2024Article
- Platinum-Catalyzed Enantioselective Diboration of Monosubstituted Alkenes.Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2024Article
- A Pyridine Dearomatization Approach for the Gram Scale Synthesis of (±)-Sparteine.Organic letters · 2023Article
- Sparteine-Free, Highly Stereoselective Construction of Complex Allylic Alcohols Using 1,2-Metallate Rearrangements.JACS Au · 2023Article
- Dual Nickel/Photoredox-Catalyzed Site-Selective Cross-Coupling of 1,2-Bis-Boronic Esters Enabled by 1,2-Boron Shifts.Angewandte Chemie (International ed. in English) · 2022Article
- Total Synthesis of (-)-Bastimolide A: A Showcase for Type I Anion Relay Chemistry.Angewandte Chemie (International ed. in English) · 2022Article
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6 authors.
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Abstract
Bastimolide B is a polyhydroxy macrolide isolated from marine cyanobacteria displaying antimalarial activity. It features a dense array of hydroxylated stereogenic centers with 1,5-relationships along a hydrocarbon chain. These 1,5-polyols represent a particularly challenging motif for synthesis, as the remote position of the stereocenters hampers stereocontrol. Herein, we present a strategy for 1,5-polyol stereocontrolled synthesis based on iterative boronic ester homologation with enantiopure magnesium carbenoids. By merging boronic ester homologation and transition-metal-catalyzed alkene hydroboration and diboration, the acyclic backbone of bastimolide B was rapidly assembled from readily available building blocks with full control over the remote stereocenters, enabling the total synthesis to be completed in 16 steps (LLS).
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