ArticleAngewandte Chemie (International ed. in English)2014
Improving physical properties via C-H oxidation: chemical and enzymatic approaches.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed.
- Iron-Catalyzed Dealkenylative Borylation of Alkenes via Ozonolysis.Journal of the American Chemical Society · 2026Article
- Catalyst-controlled site-selective dehydrogenation, a stepping stone for C-H oxidations in complex terpenes synthesis.Nature communications · 2026Article
- Substitution, Elimination, and Integration of Methyl Groups in Terpenes Initiated by C-H Bond Functionalization.ACS central science · 2024Article
- Synthesis and preliminary cytotoxicity evaluation of water soluble pentacyclic triterpenoid phosphonates.Scientific reports · 2024Article
- Iridium-Catalyzed, Site-Selective Silylation of Secondary C(spJournal of the American Chemical Society · 2023Article
- Allylic hydroxylation of enones useful for the functionalization of relevant drugs and natural products.Nature communications · 2023Article
- Stereoselective Epoxidation of Triterpenic Allylic Alcohols and Cytotoxicity Evaluation of Synthesized Compounds.Molecules (Basel, Switzerland) · 2023Article
- Novel Strategies in C-H Oxidations for Natural Product Diversification-A Remote Functionalization Application Summary.Frontiers in chemistry · 2021Review
- Site-selective C-H hydroxylation of pentacyclic triterpenoids directed by transient chiral pyridine-imino groups.Nature communications · 2020Article
- Late-Stage Diversification of Natural Products.ACS central science · 2020Review
- Diversity-oriented synthesis of 17-spirosteroids.Beilstein journal of organic chemistry · 2020Article
- Synthesis, cytotoxicity and anti-inflammatory activity of rhamnose-containing ursolic and betulinic acid saponins.RSC advances · 2019Article
- Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae.Journal of the American Chemical Society · 2019Article
- Iridium-Catalyzed Silylation of Unactivated C-H Bonds.Tetrahedron · 2019Article
- Second Generation Inhibitors of HIV-1 Maturation.ACS medicinal chemistry letters · 2019Article
- Selective Heteroaryl N-Oxidation of Amine-Containing Molecules.Organic letters · 2018Article
- Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the Synthesis of 1,4-Diols.Journal of the American Chemical Society · 2018Article
- Natural products as inspiration for the development of new synthetic methods.Journal of the Chinese Chemical Society. Zhongguo hua xue hui (Taipei, Taiwan) · 2018Article
- Article
- Synthesis of Diverse 11- and 12-Membered Macrolactones from a Common Linear Substrate Using a Single Biocatalyst.ACS central science · 2017Article
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Authors and funding
10 authors.
Funding
Abstract
Physicochemical properties constitute a key factor for the success of a drug candidate. Whereas many strategies to improve the physicochemical properties of small heterocycle-type leads exist, complex hydrocarbon skeletons are more challenging to derivatize because of the absence of functional groups. A variety of C-H oxidation methods have been explored on the betulin skeleton to improve the solubility of this very bioactive, yet poorly water-soluble, natural product. Capitalizing on the innate reactivity of the molecule, as well as the few molecular handles present on the core, allowed oxidations at different positions across the pentacyclic structure. Enzymatic oxidations afforded several orthogonal oxidations to chemical methods. Solubility measurements showed an enhancement for many of the synthesized compounds.
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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.