ArticleJournal of the American Chemical Society2019
Total Synthesis of (+)-Arborisidine.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 61 citations in OpenAlex.
- Review
- Mono- vs. Bis-Guanyl Hydrazone-Decorated Tricyclic Scaffolds: Effects on G-Quadruplex Binding and Selectivity.International journal of molecular sciences · 2026Article
- An overview: total synthesis of arborisidine, and arbornamine.Molecular diversity · 2025Review
- Accessing the synthesis of natural products and their analogues enabled by the Barbier reaction: a review.RSC advances · 2024Review
- Kinetics of H· Transfer from CpCr(CO)JACS Au · 2023Article
- Short, Scalable Access to Pyrrovobasine.JACS Au · 2023Article
- Dearomative logic in natural product total synthesis.Natural product reports · 2022Review
- Assembling the carbon skeleton of A-74528.Chemical science · 2022Article
- Asymmetric total synthesis of (1RSC advances · 2022Article
- Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines.Journal of the American Chemical Society · 2021Article
- Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride.Journal of the American Chemical Society · 2021Article
- Synthesis of aza-quaternary centersChemical science · 2021Article
- Asymmetric Biocatalytic Synthesis of 1-Aryltetrahydro-β-carbolines Enabled by "Substrate Walking".Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Acyclic nitronate olefin cycloaddition (ANOC): regio- and stereospecific synthesis of isoxazolines.Chemical science · 2020Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The first total synthesis of arborisidine, a unique Kopsia indole alkaloid possessing a fully substituted cyclohexanone ring system with two quaternary carbons, has been achieved in seven steps in racemic format from tryptamine and in nine steps in asymmetric format from d-tryptophan methyl ester. Key elements of the design include a carefully orchestrated decyanation protocol to finalize the asymmetric formation of an aza-quaternary center that is challenging to access in optically active format via direct Pictet-Spengler cyclizations with tryptamine, a metal-promoted 6- endo-dig cyclization of an enyne to establish the second core quaternary center, and regiospecific functionalizations of the resultant complex diene to finalize the target structure. The distinct and efficient nature of the developed solution is highlighted by several unsuccessful approaches and unexpected rearrangements.
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Registered trials
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.