ArticleJournal of the American Chemical Society2015
A synthesis of alsmaphorazine B demonstrates the chemical feasibility of a new biogenetic hypothesis.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 74 citations in OpenAlex.
- Collective asymmetric synthesis of the Strychnos alkaloids via thiophene S,S-dioxide cycloadditions.Nature chemistry · 2026Article
- Intramolecular N-O Bond Formation for the Synthesis ofJournal of the American Chemical Society · 2025Article
- Heterocyclic Surgery for Isotopic Labeling.Synlett : accounts and rapid communications in synthetic organic chemistry · 2025Article
- Discovery of Potent Kappa Opioid Receptor Agonists Derived from Akuammicine.Journal of medicinal chemistry · 2024Article
- Synthesis ofOrganic letters · 2024Article
- A bridged backbone strategy enables collective synthesis of strychnan alkaloids.Nature chemistry · 2023Article
- A Synthesis of Alstonlarsine A via Alstolucines B and F Demonstrates the Chemical Feasibility of a Proposed Biogenesis.Angewandte Chemie (International ed. in English) · 2023Article
- Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions.Beilstein journal of organic chemistry · 2023Article
- Hypeisoxazole A, a Racemic Pair of Tetrahydroisoxazole-Fused Benzylisoquinoline Alkaloids fromOrganic letters · 2022Article
- Skeletal remodeling of chalcone-based pyridinium salts to access isoindoline polycycles and their bridged derivatives.Chemical science · 2021Article
- Synthesis of tetracyclic spiroindolines by an interrupted Bischler-Napieralski reaction: total synthesis of akuammicine.Organic & biomolecular chemistry · 2021Article
- Enantioselective total syntheses of (+)-stemofoline and three congeners based on a biogenetic hypothesis.Nature communications · 2020Article
- Total Synthesis of (±)-Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen-Oxygen Bonds.Angewandte Chemie (International ed. in English) · 2020Article
- Proline-promoted dehydroxylation of α-ketols.Chemical science · 2019Article
- A three enzyme system to generate the Strychnos alkaloid scaffold from a central biosynthetic intermediate.Nature communications · 2017Article
- A Sequential Cycloaddition Strategy for the Synthesis of Alsmaphorazine B Traces a Path Through a Family ofTetrahedron · 2017Article
- Recent Advances in Substrate-Controlled Asymmetric Cyclization for Natural Product Synthesis.Molecules (Basel, Switzerland) · 2017Review
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
An N-oxide fragmentation/hydroxylamine oxidation/intramolecular 1,3-dipolar cycloaddition cascade efficiently converted an oxidized congener of akuammicine into the complex, hexacyclic architecture of the alsmaphorazine alkaloids. This dramatic structural change shows the chemical feasibility of our novel proposal for alsmaphorazine biogenesis. Critical to these endeavors was a marked improvement in our previously reported Zincke aldehyde cycloaddition approach to indole alkaloids, which permitted the gram-scale synthesis of akuammicine. The chemoselective oxidations of akuammicine leading up to the key rearrangement also generated several biogenetically related alkaloids of the alstolucine and alpneumine families.
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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.