Synthesis of 7,6-Spirocyclic Imine with Butenolide Ring Provides Evidence for the Relative Configuration of Marine Toxin 13-desMe Spirolide C
Author:
Affiliation:
1. Department of Chemistry, Faculty of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan
2. Research Promotion Institute, Oita University, 1-1 Idaigaoka, Hasama, Yufu, Oita 879-5593, Japan
Funder
Japan Society for the Promotion of Science
Publisher
American Chemical Society (ACS)
Subject
Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry
Link
https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.9b03373
Reference41 articles.
1. Spirolides B and D, two novel macrocycles isolated from the digestive glands of shellfish
2. Spirolide composition of micro-extracted pooled cells isolated from natural plankton assemblages and from cultures of the dinoflagellateAlexandrium ostenfeldii
3. Association of the gonyaulacoid dinoflagellate Alexandrium ostenfeldii with spirolide toxins in size-fractionated plankton
4. Assignment of the relative stereochemistry of the spirolides, macrocyclic toxins isolated from shellfish and from the cultured dinoflagellate Alexandrium ostenfeldii
5. Characterization of Spirolides A, C, and 13-Desmethyl C, New Marine Toxins Isolated from Toxic Plankton and Contaminated Shellfish
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1. Stereoselective synthesis of the spirocyclic core of 13-desmethyl spirolide C using an aza-Claisen rearrangement and an exo-selective Diels–Alder cycloaddition;Organic & Biomolecular Chemistry;2023
2. Metathesis Reactions in Natural Product Fragments and Total Syntheses;Asian Journal of Organic Chemistry;2022-02-23
3. Marine natural products;Natural Product Reports;2021
4. In Silico Modeling of Spirolides and Gymnodimines: Determination of S Configuration at Butenolide Ring Carbon C-4;Toxins;2020-10-29
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