ArticleNature chemistry2018
Synthetic nat- or ent-steroids in as few as five chemical steps from epichlorohydrin.
Article in Nature chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
15 citing papers in PubMed, 38 citations in OpenAlex.
- An Estrogen Receptor β Agonist with AR Antagonist Activity from a Modern AsymmetricACS medicinal chemistry letters · 2025Article
- Asymmetric Total Syntheses of Euphol and Tirucallol.Organic letters · 2023Article
- Neurosteroid enantiomers as potentially novel neurotherapeutics.Neuroscience and biobehavioral reviews · 2023Review
- The Quest for Secondary Pharmaceuticals: Drug Repurposing/Chiral-Switches Combination Strategy.ACS pharmacology & translational science · 2023Review
- Toward the Asymmetric de Novo Synthesis of Lanostanes: Construction of 7,11-Dideoxy-ΔThe Journal of organic chemistry · 2022Article
- Toward the Asymmetric Synthesis of Cardenolides and Related Steroidal Systems:Organic letters · 2022Article
- Progress toward the De Novo Asymmetric Synthesis of Euphanes.Organic letters · 2022Article
- From anOrganic letters · 2021Article
- Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.European journal of organic chemistry · 2020Article
- Diversity-oriented synthesis of 17-spirosteroids.Beilstein journal of organic chemistry · 2020Article
- A general strategy for diversifying complex natural products to polycyclic scaffolds with medium-sized rings.Nature communications · 2019Article
- A synthesis strategy for tetracyclic terpenoids leads to agonists of ERβ.Nature communications · 2019Article
- Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation.Journal of the American Chemical Society · 2019Article
- Transient [3,3] Cope rearrangement of 3,3-dicyano-1,5-dienes: computational analysis and 2-step synthesis of arylcycloheptanes.Chemical science · 2018Article
- Synthesis and Discovery of Estra-1,3,5(10),6,8-pentaene-2,16α-diol.Organic letters · 2018Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Today, more than 100 Food and Drug Administration-approved steroidal agents are prescribed daily for indications including heart failure, inflammation, pain and cancer. While triumphs in organic chemistry have enabled the establishment and sustained growth of the steroid pharmaceutical industry, the production of highly functionalized synthetic steroids of varying substitution and stereochemistry remains challenging, despite the numerous reports of elegant strategies for their de novo synthesis. Here, we describe an advance in chemical synthesis that has established an enantiospecific means to access novel steroids with unprecedented facility and flexibility through the sequential use of two powerful ring-forming reactions: a modern metallacycle-mediated annulative cross-coupling and a new acid-catalysed vinylcyclopropane rearrangement cascade. In addition to accessing synthetic steroids of either enantiomeric series, these steroidal products have been selectively functionalized within each of the four carbocyclic rings, a synthetic ent-steroid has been prepared on a multigram scale, the enantiomer of a selective oestrogen has been synthesized, and a novel ent-steroid with growth inhibitory properties in three cancer cell lines has been discovered.
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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.