ArticleAngewandte Chemie (International ed. in English)2016
Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 58 citations in OpenAlex.
- Total Synthesis of Daphnepapytone A.The Journal of organic chemistry · 2025Article
- Gram-Scale Access to (3,11)-Cyclotaxanes-Synthesis of 1-Hydroxytaxuspine C.Angewandte Chemie (International ed. in English) · 2025Article
- Advances, opportunities, and challenges in methods for interrogating the structure activity relationships of natural products.Natural product reports · 2024Review
- Molecular complexity as a driving force for the advancement of organic synthesis.Nature reviews. Chemistry · 2024Review
- Article
- Total syntheses of Tetrodotoxin and 9-epiTetrodotoxin.Nature communications · 2024Article
- Late-Stage Diversification: A Motivating Force in Organic Synthesis.Journal of the American Chemical Society · 2021Article
- Bridging the gap between natural product synthesis and drug discovery.Natural product reports · 2020Review
- Two-Phase Synthesis of Taxol.Journal of the American Chemical Society · 2020Article
- Asymmetric Total Syntheses of Di- and Sesquiterpenoids by Catalytic C-C Activation of Cyclopentanones.Angewandte Chemie (International ed. in English) · 2020Article
- Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.Journal of the American Chemical Society · 2019Article
- Divergent synthesis of thapsigargin analogs.Bioorganic & medicinal chemistry letters · 2018Article
- Sustainable Syntheses of (-)-Jerantinines A & E and Structural Characterisation of the Jerantinine-Tubulin Complex at the Colchicine Binding Site.Scientific reports · 2018Article
- Total Syntheses of (-)-Majucin and (-)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes.Journal of the American Chemical Society · 2017Article
- Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.Chemical reviews · 2017Review
- Article
- Fe-Catalyzed C-C Bond Construction from Olefins via Radicals.Journal of the American Chemical Society · 2017Article
- Scalable Synthesis of (-)-Thapsigargin.ACS central science · 2017Article
- Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin.Journal of the American Chemical Society · 2016Article
- Radicals: Reactive Intermediates with Translational Potential.Journal of the American Chemical Society · 2016Review
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
In the realm of natural product chemistry, few isolates have risen to the level of fame justifiably accorded to Taxol (1) and its chemical siblings. This report describes the most concise route to date for accessing the highly oxidized members of this family. As representative members of taxanes containing five oxygen atoms, decinnamoyltaxinine E (2) and taxabaccatin III (3), have succumbed to enantioselective total synthesis for the first time in only 18 steps from a simple olefin starting material. The strategy holistically mimics nature's approach (two-phase synthesis) and features a carefully choreographed sequence of stereoselective oxidations and a remarkable redox-isomerization to set the key trans-diol present in 2 and 3. This work lays the critical groundwork necessary to access even higher oxidized taxanes such as 1 in a more practical fashion, thus empowering a medicinal chemistry campaign that is not wedded to semi-synthesis.
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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.