ArticleNature communications2020
Asymmetric total synthesis of yuzurimine-type Daphniphyllum alkaloid (+)-caldaphnidine J.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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8 citing papers in PubMed, 58 citations in OpenAlex.
- Synthesis optimization of AMolecular diversity · 2026Article
- Total synthesis of natural products facilitated by prins reaction: a review.RSC advances · 2026Review
- Total Synthesis of Calyciphylline F.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis of the Tetracyclic Core of the Daphlongeranines.Organic letters · 2025Article
- Review
- Molecular Complexity-Inspired Synthetic Strategies toward the Calyciphylline A-TypeJournal of the American Chemical Society · 2024Article
- The Latest Progress in the Chemistry ofMolecules (Basel, Switzerland) · 2024Review
- Evolution towards green radical generation in total synthesis.Chemical Society reviews · 2021Review
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Ever since Hirata's report of yuzurimine in 1966, nearly fifty yuzurimine-type alkaloids have been isolated, which formed the largest subfamily of the Daphniphyllum alkaloids. Despite extensive synthetic studies towards this synthetically challenging and biologically intriguing family, no total synthesis of any yuzurimine-type alkaloids has been achieved to date. Here, the first enantioselective total synthesis of (+)-caldaphnidine J, a highly complex yuzurimine-type Daphniphyllum alkaloid, is described. Key transformations of this approach include a highly regioselective Pd-catalyzed hydroformylation, a samarium(II)-mediated pinacol coupling, and a one-pot Swern oxidation/ketene dithioacetal Prins reaction. Our approach paves the way for the synthesis of other yuzurimine-type alkaloids and related natural products.
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