ArticleJournal of the American Chemical Society2016
Synthesis of a Potent Vinblastine: Rationally Designed Added Benign Complexity.
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 17 papers.
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Who cites it
17 citing papers in PubMed, 39 citations in OpenAlex.
- KRSC advances · 2026Article
- Article
- Efficient production of vindoline from tabersonine by metabolically engineered Saccharomyces cerevisiae.Communications biology · 2021Article
- Total synthesis of (-)-4-desacetoxy-1-oxovindoline: Single atom exchange of an embedded core heteroatom in vindoline.Tetrahedron · 2021Article
- The quest for supernatural products: the impact of total synthesis in complex natural products medicinal chemistry.Natural product reports · 2020Review
- Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes, 1-Aza-1,3-Butadienes, Cyclopropenone Ketals, and Related Systems. A Retrospective.The Journal of organic chemistry · 2019Review
- Ultra-potent vinblastine analogues improve on-target activity of the parent microtubulin-targeting compound.Bioorganic & medicinal chemistry letters · 2019Article
- Natural Products in the "Marketplace": Interfacing Synthesis and Biology.Journal of the American Chemical Society · 2019Review
- High expression of class III β-tubulin has no impact on functional cancer cell growth inhibition of a series of key vinblastine analogs.Bioorganic & medicinal chemistry letters · 2018Article
- Cobalt bis(acetylacetonate)-Beilstein journal of organic chemistry · 2018Article
- Dynamic Strategic Bond Analysis Yields a Ten-Step Synthesis of 20-nor-Salvinorin A, a Potent κ-OR Agonist.ACS central science · 2017Article
- The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry-Biology Interface.The Journal of organic chemistry · 2017Article
- Vinblastine 20' Amides: Synthetic Analogues That Maintain or Improve Potency and Simultaneously Overcome Pgp-Derived Efflux and Resistance.Journal of medicinal chemistry · 2017Article
- Key analogs of a uniquely potent synthetic vinblastine that contain modifications of the C20' ethyl substituent.Bioorganic & medicinal chemistry letters · 2017Article
- Total synthesis of a key series of vinblastines modified at C4 that define the importance and surprising trends in activity.Chemical science · 2017Article
- Ultrapotent vinblastines in which added molecular complexity further disrupts the target tubulin dimer-dimer interface.Proceedings of the National Academy of Sciences of the United States of America · 2016Article
- Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.Chemical reviews · 2016Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Many natural products, including vinblastine, have not been easily subjected to simplifications in their structures by synthetic means or modifications by late-stage semisynthetic derivatization in ways that enhance their biological potency. Herein, we detail a synthetic vinblastine that incorporates added benign complexity (ABC), which improves activity 10-fold, and is now accessible as a result of advances in the total synthesis of the natural product. The compound incorporates designed added molecular complexity but no new functional groups and maintains all existing structural and conformational features of the natural product. It constitutes a member of an analogue class presently inaccessible by semisynthetic derivatization of the natural product, by its late-stage functionalization, or by biosynthetic means. Rather, it was accessed by synthetic means, using an appropriately modified powerful penultimate single-step vindoline-catharanthine coupling strategy that proceeds with a higher diastereoselectivity than found for the natural product itself.
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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.