Total synthesis of Asperdinones B, C, D, E and Terezine D

chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry The total synthesis of new members of prenylated indole alkaloids exhibiting α-glucosidase activity is described. Asperdinones B, C, D, and E are characterized by the presence of a 10R 3-indolylmethyl benzodiazepine-2,5-dione unit at C-3 of the C4-C7 prenylated indoles. Methods of direct and indirect prenylation of indole and tryptophane were explored. Different approaches were adopted for functionalization of C4-C7 prenyl indoles at C3 using Negishi cross-coupling methods. The asperdinones are among the rare tryptophane-derived indole alkaloids which appear to have undergone epimerization due to genetic alteration of specific gene clusters that code for a C10 R configuration

Indole alkaloid; Negishi reaction;prenylation;C-H activation | Format: DOCX | Size: 28.0 MB | Download | When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information: Devarajappa, R.; Hanessian, S. Beilstein Arch. 2025, 202556. doi:10.3762/bxiv.2025.56.v1 Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below. Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero. © 2025 Devarajappa and Hanessian; licensee Beilstein-Institut. This is an open access work licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-archives.org/xiv/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this work could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.