ArticleNature communications2024
Divergent and gram-scale syntheses of (-)-veratramine and (-)-cyclopamine.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Total Synthesis of Ussuriedine via a Late-Stage Stevens Rearrangement: Implications for Biosynthesis.Journal of the American Chemical Society · 2026Article
- Divergent evolution of fungal P450 monooxygenase unlocks simultaneous access to C12β and C15α oxyfunctionalization of steroids.Nature communications · 2025Article
- Recent Advances in Bioinspired Cu-Directed C-H Hydroxylation Reactions.Accounts of chemical research · 2025Article
- Identification of genes involved in verazine biosynthesis in Veratrum grandiflorum and their heterologous production in Saccharomyces cerevisiae.BMC plant biology · 2025Article
- Recent advancements in the synthesis ofBeilstein journal of organic chemistry · 2025Review
- Divergent syntheses of complex Veratrum alkaloids.Nature communications · 2024Article
- Verazine biosynthesis from simple sugars in engineered Saccharomyces cerevisiae.Metabolic engineering · 2024Article
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Authors and funding
7 authors.
Funding
Abstract
Veratramine and cyclopamine, two of the most representative members of the isosteroidal alkaloids, are valuable molecules in agricultural and medicinal chemistry. While plant extraction of these compounds suffers from uncertain supply, efficient chemical synthesis approaches are in high demand. Here, we present concise, divergent, and scalable syntheses of veratramine and cyclopamine with 11% and 6.2% overall yield, respectively, from inexpensive dehydro-epi-androsterone. Our synthesis readily provides gram quantities of both target natural products by utilizing a biomimetic rearrangement to form the C-nor-D-homo steroid core and a stereoselective reductive coupling/(bis-)cyclization sequence to establish the (E)/F-ring moiety.
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Registered trials
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