{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T19:43:33Z","timestamp":1792784613845,"version":"4.5.0"},"reference-count":22,"publisher":"American Chemical Society (ACS)","issue":"41","license":[{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100004794","name":"Centre National de la Recherche Scientifique","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100004794","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"French Research Ministry, Aix-Marseille University","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"},{"id":"https:\/\/ror.org\/035xkbk20","id-type":"ROR","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Pandanus amaryllifolius produces structurally unique alkaloids, including pandanusines A and B and pandamarine, featuring rare diazaspirocyclic \u03b3-lactam frameworks. Herein, we report concise total syntheses of these three natural products based on a modular copper(I)-catalyzed reaction. Readily accessible \u03b3-hydroxy-\u03b3-lactams were prepared from iodoacrylic acids, terminal alkynes, and primary amines and subsequently transformed through N-acyliminium ion intermediates to construct diazaspirocyclic backbones. This strategy enabled the synthesis of (\u00b1)-pandanusine B in four steps (40% overall yield) and (\u00b1)-pandanusine A in five steps (26.5% overall yield) after optimization of the protecting group strategy. The methodology was further extended to the total synthesis of the more complex alkaloid pandamarine. These results demonstrate the synthetic potential of \u03b3-hydroxy-\u03b3-lactams as versatile precursors for the rapid construction of architecturally complex alkaloid scaffolds. Furthermore, the absolute configurations of both HPLC-separated enantiomers of pandanusine A and B were unambiguously determined through a combination of vibrational and electronic circular dichroism analyses and DFT and TD-DFT calculations.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01791","type":"journal-article","created":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T18:02:35Z","timestamp":1790791355000},"page":"13724-13734","source":"Crossref","is-referenced-by-count":0,"title":["Modular Strategy\nfor the Collective Total Synthesis\nof\n                    <i>Pandanus amaryllifolius<\/i>\n                    Alkaloids: Pandanusines\nA and B and Pandamarine"],"prefix":"10.1021","volume":"91","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-3139-8179","authenticated-orcid":true,"given":"Edouard","family":"Fauran","sequence":"first","affiliation":[{"name":"Aix Marseille Univ, CNRS, Centrale Med, ISM2 , ,","place":["Marseille, France, 13397"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8523-4476","authenticated-orcid":true,"given":"Jean-Vale\u0300re","family":"Naubron","sequence":"additional","affiliation":[{"name":"Aix Marseille Univ, CNRS, Centrale Med, FSCM , ,","place":["Marseille, France, 13397"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4331-6198","authenticated-orcid":true,"given":"Laurent","family":"Commeiras","sequence":"additional","affiliation":[{"name":"Aix Marseille Univ, CNRS, Centrale Med, ISM2 , ,","place":["Marseille, France, 13397"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,30]]},"reference":[{"key":"2026101608082013000_cit1","doi-asserted-by":"publisher","first-page":"106144","DOI":"10.1016\/j.fitote.2024.106144","article-title":"Botany, phytochemistry, pharmacology, and applications\nof Pandanus amaryllifolius Roxb.: A review","volume":"177","author":"Wang","year":"2024","journal-title":"Fitoterapia"},{"key":"2026101608082013000_cit2a","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/bs.alkal.2018.12.001","article-title":"Recent Progress in\nthe Chemistry\nof Pandanus Alkaloids","volume":"82","author":"Tan","year":"2019","journal-title":"Alkaloids: Chem. Biol."},{"key":"2026101608082013000_cit2b","doi-asserted-by":"publisher","first-page":"215","DOI":"10.1016\/S1099-4831(08)00204-6","article-title":"Pandanus Alkaloids:\nChemistry and Biology","volume":"66","author":"Nonato","year":"2008","journal-title":"Alkaloids: Chem. Biol."},{"key":"2026101608082013000_cit3","doi-asserted-by":"publisher","first-page":"3423","DOI":"10.1016\/j.tet.2017.05.002","article-title":"Isolation and absolute\nconfiguration determination of alkaloids from","volume":"73","author":"Cheng","year":"2017","journal-title":"Pandanus amaryllifolius. Tetrahedron"},{"key":"2026101608082013000_cit4","doi-asserted-by":"publisher","first-page":"1903","DOI":"10.1071\/CH9921903","article-title":"The X-Ray Crystal-Structure\nof (+\/-)-Pandamarine, the\nMajor Alkaloid of Pandanus amaryllifolius","volume":"45","author":"Byrne","year":"1992","journal-title":"Aust. J. Chem."},{"key":"2026101608082013000_cit5a","doi-asserted-by":"publisher","first-page":"543","DOI":"10.1002\/adsc.201500994","article-title":"Copper(I)-Catalysed\nMulticomponent Reaction: Straightforward Access to 5-Hydroxy-1H-pyrrol-2(5H)-ones","volume":"358","author":"Mardjan","year":"2016","journal-title":"Adv. Synth. Catal"},{"key":"2026101608082013000_cit5b","doi-asserted-by":"publisher","first-page":"606","DOI":"10.1021\/acs.oprd.9b00438","article-title":"Straightforward Access to a Great Diversity of Complex\nBiorelevant \u03b3-Lactams Thanks to a Tunable Cascade Multicomponent\nProcess","volume":"24","author":"Mardjan","year":"2020","journal-title":"Org. Process Res. Dev."},{"key":"2026101608082013000_cit6a","doi-asserted-by":"publisher","first-page":"3304","DOI":"10.1039\/C7OB00532F","article-title":"Tunable Copper-Catalyzed Multicomponent Reaction Towards\nAlkaloid-Inspired Indole\/Lactam Polycycles","volume":"15","author":"Mardjan","year":"2017","journal-title":"Org. Biomol. Chem."},{"key":"2026101608082013000_cit6b","doi-asserted-by":"publisher","first-page":"5298","DOI":"10.1021\/acs.orglett.2c01898","article-title":"Enantioselective\nConstruction of Tetrasubstituted Carbon Stereocenters via Chiral Phosphoric\nAcid-Catalyzed Friedel\u2013Craft Alkylation of Indoles with 5-Substituted\nHydroxybutyrolactams","volume":"24","author":"Saidah","year":"2022","journal-title":"Org. Lett."},{"key":"2026101608082013000_cit7a","doi-asserted-by":"publisher","first-page":"5467","DOI":"10.1021\/acs.orglett.9b01727","article-title":"Singlet-Oxygen-Mediated\nSynthesis\nof Pandanusine A and Pandalizine C and Structural Revision of Pandanusine\nB","volume":"21","author":"Kalaitzakis","year":"2019","journal-title":"Org. Lett."},{"key":"2026101608082013000_cit7b","doi-asserted-by":"publisher","first-page":"3596","DOI":"10.1021\/acs.orglett.5b01693","article-title":"First Total\nSynthesis of Pandamarine","volume":"17","author":"Kalaitzakis","year":"2015","journal-title":"Org. Lett."},{"key":"2026101608082013000_cit8a","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2200814119","article-title":"Convergent\nTotal Synthesis of (+)-Calcipotriol: A Scalable, Modular Approach\nto Vitamin D Analogs","volume":"119","author":"Gu","year":"2022","journal-title":"Proc. Natl. Acad. Sci.\nU. S. A."},{"key":"2026101608082013000_cit8b","doi-asserted-by":"publisher","first-page":"2919","DOI":"10.1039\/D6QO00050A","article-title":"Oxidation reactions\nin the current total synthesis of natural products","volume":"13","author":"Zheng","year":"2026","journal-title":"Org. Chem. Front."},{"key":"2026101608082013000_cit9","doi-asserted-by":"publisher","first-page":"7345","DOI":"10.1021\/acs.orglett.8b03345","article-title":"Photocatalytic Oxyamination\nof Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis","volume":"20","author":"Reed","year":"2018","journal-title":"Org. 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Catal."},{"key":"2026101608082013000_cit14b","doi-asserted-by":"publisher","first-page":"13692","DOI":"10.1002\/chem.201102570","article-title":"Carboxylate-Directed Tandem Functionalisations\nof \u03b1,\u03b2-Dihaloalkenoic Acids with 1-Alkynes: A Straightforward\nAccess to (Z)-Configured, \u03b1,\u03b2-Substituted \u03b3-Alkylidenebutenolides","volume":"17","author":"Inack-Ngi","year":"2011","journal-title":"Chem. - Eur. 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