Academic Journal
Total Synthesis of (−)-Amovillosumin A and Structure Correction of (−)-Amovillosumin C Using Chemical Synthesis
| العنوان: | Total Synthesis of (−)-Amovillosumin A and Structure Correction of (−)-Amovillosumin C Using Chemical Synthesis |
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| المؤلفون: | Kim, Irene Jeongin, Pilkington, Lisa I, Barker, David |
| بيانات النشر: | American Chemical Society (ACS) |
| سنة النشر: | 2024 |
| المجموعة: | University of Auckland Research Repository - ResearchSpace |
| مصطلحات موضوعية: | 03 Chemical Sciences, 06 Biological Sciences, 11 Medical and Health Sciences, 4208 Traditional, complementary and integrative medicine |
| الوصف: | Norlignans are a rare class of natural products isolated from a diverse range of plant species, many of which have interesting biological activities including antibacterial, antioxidant, phytotoxic, platelet aggregation inhibitory effects, and more. Isolated from Amomum villosum (Amomi Fructus), amovillosumins A (1) and C (3) are norlignans which were of interest to synthesize, due to their interesting bioactivities, specifically their ability to increase stimulation of glucagon-like peptide-1 (GLP-1) secretion. In this research, key intermediate 15 was used to stereoselectively synthesize (7R,8R)-amovillosumins A (1) and C (3). The developed method includes a Mitsunobu coupling, a modified rhodium-catalyzed Miyaura arylation, and an acid-catalyzed cyclization in key bond-forming steps. After synthesis, the structure of 1 was confirmed, but it was revealed that the benzodioxane-containing structure of amovillosumin C (3) that had been proposed in the literature was incorrect. Thus, with further investigation a structure correction of 3 was achieved by synthesis, the correct structure being 8-O-4′-oxynorlignan. |
| نوع الوثيقة: | article in journal/newspaper |
| وصف الملف: | application/pdf |
| اللغة: | English |
| تدمد: | 0163-3864 1520-6025 |
| Relation: | Journal of Natural Products; (2024). Journal of natural products 87(2) 340–348.; https://hdl.handle.net/2292/67566 |
| DOI: | 10.1021/acs.jnatprod.3c01069 |
| الاتاحة: | https://hdl.handle.net/2292/67566 https://doi.org/10.1021/acs.jnatprod.3c01069 |
| Rights: | Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. ; https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm ; Copyright: 2024 American Chemical Society and American Society of Pharmacognosy ; http://purl.org/eprint/accessRights/RetrictedAccess |
| رقم الانضمام: | edsbas.D7ED6973 |
| قاعدة البيانات: | BASE |
| تدمد: | 01633864 15206025 |
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| DOI: | 10.1021/acs.jnatprod.3c01069 |