ArticleProceedings of the National Academy of Sciences of the United States of America2022
Convergent total synthesis of (+)-calcipotriol: A scalable, modular approach to vitamin D analogs.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Vitamin D in Photosynthetic Organisms and Fungi: Sterol Photochemistry, UV-B Availability, and Biofortification Potential.Current issues in molecular biology · 2026Review
- Highly selective aldehyde coupling on the heterointerface of molybdenum selenide and graphdiyne.Science advances · 2025Article
- Synthesis, Molecular Docking and Biological Evaluation of A-Ring-Carborane-Vitamin D Analogues.Molecules (Basel, Switzerland) · 2025Article
- Recent Advancements Towards the Use of Vitamin D Isoforms and the Development of Their Synthetic Analogues as New Therapeutics.Biomedicines · 2025Review
- Modified Working Electrodes for Organic Electrosynthesis.ACS organic & inorganic Au · 2024Review
- Directed Hydrogen Atom Transfer for Selective Reactions of Polyenols.Journal of the American Chemical Society · 2024Article
- Chemoenzymatic synthesis of optically active α-cyclopropyl-pyruvates and cyclobutenoates via enzyme-catalyzed carbene transfer with diazopyruvate.Organic chemistry frontiers : an international journal of organic chemistry · 2024Article
- Mechanisms for radical reactions initiating fromBeilstein journal of organic chemistry · 2024Article
- Studies towards the Synthesis of (+)-Dictyoxetane.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Synthesis of Deuterium-Labeled Vitamin D Metabolites as Internal Standards for LC-MS Analysis.Molecules (Basel, Switzerland) · 2022Article
- Modular terpene synthesis enabled by mild electrochemical couplings.Science (New York, N.Y.) · 2022Article
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Authors and funding
11 authors.
Funding
Abstract
A convergent approach for the total synthesis of calcipotriol (brand name: Dovonex), a proven vitamin D analog used for the treatment of psoriasis, and medicinally relevant synthetic analogs is described. A complete approach, not wedded to semisynthesis, toward both the A-ring and CD-ring is reported. From a retrosynthetic standpoint, hidden symmetry within the decorated A-ring is disclosed, which allowed for scalable quantities of this advanced intermediate. In addition, a radical retrosynthetic approach is described, which highlights an electrochemical reductive coupling as well as an intramolecular hydrogen atom transfer Giese addition to establish the 6,5-transcarbon skeleton found in the vitamin D family. Finally, a late-stage decarboxylative cross-coupling approach allowed for the facile preparation of various C20-arylated derivatives that show promising biological activity in an initial bioassay.
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