ArticleJournal of the American Chemical Society2019
A Domino 10-Step Total Synthesis of FR252921 and Its Analogues, Complex Macrocyclic Immunosuppressants.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
What it found
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Who cites it
10 citing papers in PubMed, 28 citations in OpenAlex.
- Target-agnostic SAR mapping and immunological evaluation of (-)-FR252921 and analogs against primary human immune cells.Chemical science · 2026Article
- Carbene-catalytic enantioselective synthesis of chiral macrocycles.Chemical science · 2025Review
- Cyclization by Intramolecular Suzuki-Miyaura Cross-Coupling-A Review.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Facile construction of 2-pyrones under carbene catalysis.RSC advances · 2024Review
- Ni-Catalyzed Stereoconvergent Reductive Dimerization of Bromocyclobutenes.Organic letters · 2024Article
- Late-Stage Modification of Medicine: Pd-Catalyzed Direct Synthesis and Biological Evaluation ofACS omega · 2021Article
- Ni/Pd-catalyzed Suzuki-Miyaura cross-coupling of alcohols and aldehydes and C-N cross-coupling of nitro and aminesRSC advances · 2020Article
- Unconventional Macrocyclizations in Natural Product Synthesis.ACS central science · 2020Review
- Dewar Heterocycles as Versatile Monomers for Ring-Opening Metathesis Polymerization.ACS macro letters · 2020Article
- Palladium-Catalyzed Synthesis and Anticancer Activity of Paclitaxel-Dehydroepiandrosterone Hybrids.ACS omega · 2020Article
Corrections and comments
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
Abstract
FR252921, FR252922, and FR256523 are a family of potent macrocyclic polyene immunosuppressive agents with a novel mode of action. However, the lack of an efficient and flexible synthesis has hindered further biological studies, mostly due to the fact that the natural products appear to be kinetic isomers regarding the triene moiety. Herein, we report the development and application of an unprecedented, unique domino Suzuki-Miyaura/4π-electrocyclic ring-opening macrocyclization, resulting in a concise, unified, and stereoselective synthetic route to these complex targets in only 10 steps. This in turn enables ready access to a range of unnatural analogues, among which several compounds showed inhibition of T-lymphocyte proliferation at levels equal or superior to those of the natural products themselves.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.