ArticleNature communications2018
Reagent-controlled regiodivergent ring expansions of steroids.
Article in Nature communications, 2018. 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.
- Solvent-Controlled Regiodivergent Friedel-Crafts Reactions of 1-Naphthol with In Situ Generated Aza-The Journal of organic chemistry · 2025Article
- Substitution, Elimination, and Integration of Methyl Groups in Terpenes Initiated by C-H Bond Functionalization.ACS central science · 2024Article
- Chloroformate-mediated ring cleavage of indole alkaloids leads to re-engineered antiplasmodial agents.Organic & biomolecular chemistry · 2024Article
- Regiodivergent Ring-Expansion of Oxindoles to Quinolinones.Journal of the American Chemical Society · 2024Article
- Skeletal diversification by C-C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate.Chemical communications (Cambridge, England) · 2023Article
- Revisiting the bromination of 3β-hydroxycholest-5-ene with CBrBeilstein journal of organic chemistry · 2023Article
- Azoarene activation for Schmidt-type reaction and mechanistic insights.Nature communications · 2022Article
- Ring Distortion of Vincamine Leads to the Identification of Re-Engineered Antiplasmodial Agents.ACS omega · 2021Article
- Limonin as a Starting Point for the Construction of Compounds with High Scaffold Diversity.Angewandte Chemie (International ed. in English) · 2021Article
- Preventing Morphine-Seeking Behavior through the Re-Engineering of Vincamine's Biological Activity.Journal of medicinal chemistry · 2020Article
- Intramolecular CspChemical science · 2020Article
- Re-Engineering of Yohimbine's Biological Activity through Ring Distortion: Identification and Structure-Activity Relationships of a New Class of Antiplasmodial Agents.ACS infectious diseases · 2020Article
- Diversity-oriented synthesis of 17-spirosteroids.Beilstein journal of organic chemistry · 2020Article
- Catalytic, transannular carbonyl-olefin metathesis reactions.Chemical science · 2019Article
- A general strategy for diversifying complex natural products to polycyclic scaffolds with medium-sized rings.Nature communications · 2019Article
- Diverse compounds from pleuromutilin lead to a thioredoxin inhibitor and inducer of ferroptosis.Nature chemistry · 2019Article
- Preparation of Structurally Diverse Compounds from the Natural Product Lycorine.Organic letters · 2018Article
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Authors and funding
2 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Ring expansion provides a powerful way of introducing a heteroatom substituent into a carbocyclic framework. However, such reactions are often limited by the tendency of a given substrate to afford only one of the two rearrangement products or fail to achieve high selectivity at all. These limitations are particularly acute when seeking to carry out late-stage functionalization of natural products as starting points in drug discovery. In this work, we present a stereoelectronically controlled ring expansion sequence towards selective and flexible access to complementary ring systems derived from common steroidal substrates. Chemical diversification of the reaction intermediate affords over 100 isomerically pure analogs with spatial and functional diversity. This regiodivergent rearrangement, and the concept of using chiral reagents to affect regiocontrol in chiral natural products, should be broadly applicable to late-stage natural product diversification programs.
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