{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T15:02:51Z","timestamp":1786719771687,"version":"build-2736575974"},"reference-count":42,"publisher":"American Chemical Society (ACS)","issue":"32","license":[{"start":{"date-parts":[[2026,8,3]],"date-time":"2026-08-03T00:00:00Z","timestamp":1785715200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,3]],"date-time":"2026-08-03T00:00:00Z","timestamp":1785715200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,3]],"date-time":"2026-08-03T00:00:00Z","timestamp":1785715200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100006733","name":"Indiana University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100006733","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["R35GM131755"],"award-info":[{"award-number":["R35GM131755"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"name":"SpiroChem AG"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,14]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Norbornanes are important scaffolds in organic chemistry that have been used as synthetic intermediates and as core scaffolds in drugs. These are commonly prepared by Diels\u2013Alder cycloaddition of cyclopentadiene and an alkene. While useful, the synthesis of bridgehead substitutions can be challenging. In this work, a photochemical strain-release cycloaddition of a housane and alkenes is disclosed to prepare bridgehead-substituted norbornanes. The reaction proceeds through energy-transfer activation of naphthyl-substituted housane and enables direct access to substitution patterns that are difficult to obtain through conventional approaches. A broad range of alkenes and alkynes is tolerated under the mild reaction conditions, providing a modular entry into structurally diverse norbornanes.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c02514","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T14:35:48Z","timestamp":1785854148000},"page":"10231-10235","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of\nNorbornanes via Photosensitized Strain-Release\nCycloaddition of Housane"],"prefix":"10.1021","volume":"28","author":[{"given":"Yu-Che","family":"Chang","sequence":"first","affiliation":[{"name":"Indiana University , , 800 E. Kirkwood Ave. , , ,","place":["Bloomington, Indiana, United States, 47405"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6838-3605","authenticated-orcid":true,"given":"Renyu","family":"Guo","sequence":"additional","affiliation":[{"name":"Indiana University , , 800 E. Kirkwood Ave. , , ,","place":["Bloomington, Indiana, United States, 47405"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alberto","family":"Najera","sequence":"additional","affiliation":[{"name":"Indiana University , , 800 E. Kirkwood Ave. , , ,","place":["Bloomington, Indiana, United States, 47405"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas","family":"Fessard","sequence":"additional","affiliation":[{"name":"SpiroChem AG , Rosental area, WRO-1047-3, Mattenstrasse 22 , ,","place":["Basel, Switzerland, 4058"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9668-8134","authenticated-orcid":true,"given":"Christophe","family":"Salome","sequence":"additional","affiliation":[{"name":"SpiroChem AG , Rosental area, WRO-1047-3, Mattenstrasse 22 , ,","place":["Basel, Switzerland, 4058"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4993-0917","authenticated-orcid":true,"given":"M. Kevin","family":"Brown","sequence":"additional","affiliation":[{"name":"Indiana University , , 800 E. Kirkwood Ave. , , ,","place":["Bloomington, Indiana, United States, 47405"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,3]]},"reference":[{"key":"2026081410081792300_cit1","doi-asserted-by":"publisher","first-page":"9291","DOI":"10.1016\/j.tet.2009.09.018","article-title":"Norbornane as the novel pseudoglycone moiety in nucleosides","volume":"65","author":"S\u030ca\u0301la","year":"2009","journal-title":"Tetrahedron"},{"key":"2026081410081792300_cit2","doi-asserted-by":"publisher","first-page":"1887","DOI":"10.1021\/acs.jmedchem.8b01372","article-title":"New Rigid Nicotine\nAnalogues, Carrying a Norbornane Moiety, Are Potent Agonists of \u03b17\nand \u03b13* Nicotinic Receptors","volume":"62","author":"Manetti","year":"2019","journal-title":"J. Med. Chem."},{"key":"2026081410081792300_cit3","doi-asserted-by":"publisher","first-page":"1465","DOI":"10.3390\/ph15121465","article-title":"Norbornene\nand Related Structures as Scaffolds in the Search for New Cancer Treatments","volume":"15","author":"Calvo-Marti\u0301n","year":"2022","journal-title":"Pharmaceuticals"},{"key":"2026081410081792300_cit4","doi-asserted-by":"publisher","first-page":"6752","DOI":"10.1021\/jm901241e","article-title":"Escape from\nFlatland: Increasing\nSaturation as an Approach to Improving Clinical Success","volume":"52","author":"Lovering","year":"2009","journal-title":"J. Med. Chem."},{"key":"2026081410081792300_cit5","doi-asserted-by":"publisher","first-page":"215","DOI":"10.1016\/j.chempr.2018.10.017","article-title":"Providing a New Aniline Bioisostere through the Photochemical\nProduction of 1-Aminonorbornanes","volume":"5","author":"Staveness","year":"2019","journal-title":"Chem."},{"key":"2026081410081792300_cit6","doi-asserted-by":"publisher","first-page":"21","DOI":"10.1002\/med.20013","article-title":"Pharmacology and structure-activity relationships of\nbioactive polycyclic cage compounds: A focus on pentacycloundecane\nderivatives","volume":"25","author":"Geldenhuys","year":"2005","journal-title":"Med. Res. Rev."},{"key":"2026081410081792300_cit7","doi-asserted-by":"publisher","first-page":"137","DOI":"10.1007\/s00044-007-9044-5","article-title":"Medicinal chemistry\nof polycyclic cage compounds in\ndrug discovery research","volume":"17","author":"Oliver","year":"2008","journal-title":"Med. Chem. Res."},{"key":"2026081410081792300_cit8","doi-asserted-by":"publisher","first-page":"375","DOI":"10.1002\/cmdc.201100559","article-title":"Polycyclic Cage Structures as Lipophilic\nScaffolds for Neuroactive Drugs","volume":"7","author":"Joubert","year":"2012","journal-title":"ChemMedChem."},{"key":"2026081410081792300_cit9","doi-asserted-by":"publisher","first-page":"215","DOI":"10.1016\/j.chempr.2018.10.017","article-title":"Providing\na New Aniline Bioisostere through the Photochemical\nProduction of 1-Aminonorbornanes","volume":"5","author":"Staveness","year":"2019","journal-title":"Chem."},{"key":"2026081410081792300_cit10","doi-asserted-by":"publisher","first-page":"1668","DOI":"10.1002\/1521-3773(20020517)41:10&lt;1668::AID-ANIE1668&gt;3.0.CO;2-Z","article-title":"The Diels-Alder\nReaction in Total Synthesis","volume":"41","author":"Nicolaou","year":"2002","journal-title":"Angew. Chem., Int.\nEd."},{"key":"2026081410081792300_cit11","doi-asserted-by":"publisher","first-page":"4496","DOI":"10.1039\/D4RA07989B","article-title":"Recent\nadvancements in the chemistry\nof Diels-Alder reaction for total synthesis of natural products: a\ncomprehensive review (2020\u20132023)","volume":"15","author":"Rana","year":"2025","journal-title":"RSC\nAdv."},{"key":"2026081410081792300_cit12","doi-asserted-by":"publisher","first-page":"9536","DOI":"10.1021\/ja0735958","article-title":"Regioselective\nand Asymmetric Diels-Alder Reaction\nof 1- and 2-Substituted Cyclopentadienes Catalyzed by a Bro\u0337nsted\nAcid Activated Chiral Oxazaborolidine","volume":"129","author":"Payette","year":"2007","journal-title":"J. Am.\nChem. Soc."},{"key":"2026081410081792300_cit13","doi-asserted-by":"publisher","first-page":"6726","DOI":"10.1021\/jo500942a","article-title":"Sequential Diels-Alder Reaction\/Rearrangement\nSequence: Synthesis of Functionalized Bicyclo[2.2.1]heptane Derivatives\nand Revision of Their Relative Configuration","volume":"79","author":"Liang","year":"2014","journal-title":"J. Org. Chem."},{"key":"2026081410081792300_cit14","doi-asserted-by":"publisher","first-page":"13630","DOI":"10.1002\/anie.201507348","article-title":"Direct\nAccess to Multifunctionalized Norcamphor Scaffolds by Asymmetric Organocatalytic\nDiels-Alder Reactions","volume":"54","author":"Mose","year":"2015","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081410081792300_cit15","doi-asserted-by":"publisher","first-page":"5229","DOI":"10.1039\/C6OB00814C","article-title":"An asymmetric\napproach to bicyclo[2.2.1]heptane-1-carboxylates via a formal [4 +\n2] cycloaddition reaction enabled by organocatalysis","volume":"14","author":"Fu","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"2026081410081792300_cit16","doi-asserted-by":"publisher","first-page":"9123","DOI":"10.1021\/acs.orglett.1c03451","article-title":"Synthesis\nof a Bicyclo[2.2.1]heptane Skeleton with Two Oxy-Functionalized Bridgehead\nCarbons via the Diels-Alder Reaction","volume":"23","author":"Ikeuchi","year":"2021","journal-title":"Org. Lett."},{"key":"2026081410081792300_cit17","doi-asserted-by":"publisher","first-page":"77","DOI":"10.1080\/00397911.2023.2284348","article-title":"An efficient,\nconcise\nsynthetic approach to \u03b3-aminobutyric acid (GABA) derivatives\nbearing bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane rings","volume":"54","author":"Luo","year":"2024","journal-title":"Synth. Commun."},{"key":"2026081410081792300_cit18","doi-asserted-by":"publisher","first-page":"8351","DOI":"10.1038\/s41467-024-52644-4","article-title":"Facile Enantioselective\nSynthesis of Multi-Substituted\nNorbornanes\/Norbornenes Using a Latent Synthon Strategy","volume":"15","author":"Shen","year":"2024","journal-title":"Nat. Commun."},{"key":"2026081410081792300_cit19","doi-asserted-by":"publisher","first-page":"1939","DOI":"10.1016\/0040-4020(63)85008-5","article-title":"Some General\nCharacteristic Properties\nof Substituted Cyclopentadienes","volume":"19","author":"Mironov","year":"1963","journal-title":"Tetrahedron"},{"key":"2026081410081792300_cit20","doi-asserted-by":"publisher","first-page":"6777","DOI":"10.1021\/acs.chemrev.0c01055","article-title":"Click Chemistry\nwith Cyclopentadiene","volume":"121","author":"Levandowski","year":"2021","journal-title":"Chem. Rev."},{"key":"2026081410081792300_cit21","doi-asserted-by":"publisher","first-page":"41","DOI":"10.1021\/ar50098a001","article-title":"Stable\nCarbocations, 189. The Sigma-Bridged 2-Norbornyl Cation and Its Significance\nto Chemistry","volume":"9","author":"Olah","year":"1976","journal-title":"Acc. Chem. Res."},{"key":"2026081410081792300_cit22","doi-asserted-by":"publisher","first-page":"6058","DOI":"10.1021\/jo00311a028","article-title":"Preparation\nof 1-substituted bicyclo[2.2.1]heptanes\nby anionic cyclization of a 5-hexen-1-yllithium","volume":"55","author":"Bailey","year":"1990","journal-title":"J. Org. Chem."},{"key":"2026081410081792300_cit23","doi-asserted-by":"publisher","first-page":"9","DOI":"10.1038\/s42004-022-00811-3","article-title":"Bicyclobutanes as unusual building blocks for complexity\ngeneration in organic synthesis","volume":"6","author":"Golfmann","year":"2023","journal-title":"Commun. Chem."},{"key":"2026081410081792300_cit24","doi-asserted-by":"publisher","first-page":"20716","DOI":"10.1021\/jacs.3c08206","article-title":"Strain-Release Photocatalysis","volume":"145","author":"Bellotti","year":"2023","journal-title":"J. Am. Chem. Soc."},{"key":"2026081410081792300_cit25","doi-asserted-by":"publisher","first-page":"6942","DOI":"10.1039\/D4QO01741B","article-title":"State-of-the-art strategies\nfor Lewis acid-catalyzed strain-release cycloadditions of bicyclo[1.1.0]butanes\n(BCBs)","volume":"11","author":"Liu","year":"2024","journal-title":"Org. Chem. Front."},{"key":"2026081410081792300_cit26","doi-asserted-by":"publisher","first-page":"4172","DOI":"10.1002\/anie.200600723","article-title":"Pericyclic Cascade\nReactions of (Bicyclo[1.1.0]butylmethyl)amines","volume":"45","author":"Wipf","year":"2006","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081410081792300_cit27","doi-asserted-by":"publisher","first-page":"7988","DOI":"10.1021\/jacs.2c02976","article-title":"Strain-Release [2\u03c0 + 2\u03c3]\nCycloadditions for the Synthesis of Bicyclo[2.1.1]hexanes Initiated\nby Energy Transfer","volume":"144","author":"Guo","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"2026081410081792300_cit28","doi-asserted-by":"publisher","first-page":"477","DOI":"10.1038\/s41586-022-04636-x","article-title":"Intermolecular\n[2\u03c0+2\u03c3]-Photocycloaddition\nEnabled by Triplet Energy Transfer","volume":"605","author":"Kleinmans","year":"2022","journal-title":"Nature"},{"key":"2026081410081792300_cit29","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202214507","article-title":"Diboron(4)-Catalyzed Remote [3 +\n2] Cycloaddition of Cyclopropanes via Dearomative\/Rearomative Radical\nTransmission through Pyridine","volume":"61","author":"Xu","year":"2022","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026081410081792300_cit30","doi-asserted-by":"publisher","first-page":"535","DOI":"10.1038\/s41557-023-01135-y","article-title":"A Catalytic Alkene Insertion Approach\nto Bicyclo[2.1.1]hexane Bioisosteres","volume":"15","author":"Agasti","year":"2023","journal-title":"Nat. Chem."},{"key":"2026081410081792300_cit31","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202304771","article-title":"Lewis Acid\nCatalyzed Formal (3 +\n2)-Cycloaddition of Bicyclo[1.1.0]butanes with Ketenes","volume":"62","author":"Radhoff","year":"2023","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081410081792300_cit32","doi-asserted-by":"publisher","first-page":"16237","DOI":"10.1021\/jacs.4c04403","article-title":"Bicyclo[1.1.0]butyl\nRadical Cations: Synthesis and Application to [2\u03c0+2\u03c3]\nCycloaddition Reactions","volume":"146","author":"Tyler","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026081410081792300_cit33","doi-asserted-by":"publisher","first-page":"13987","DOI":"10.1021\/acscatal.4c05067","article-title":"Photocatalytic\nOxidative Activation of Bicyclo[1.1.0]butanes for Formal [2\u03c3+2\u03c0]\nCycloadditions","volume":"14","author":"Golfmann","year":"2024","journal-title":"ACS Catal."},{"key":"2026081410081792300_cit34","doi-asserted-by":"publisher","first-page":"14936","DOI":"10.1021\/jacs.5c02425","article-title":"Catalyst-Controlled\nRegiodivergent Synthesis of Bicyclo[2.1.1]hexanes via Photochemical\nStrain-Release Cycloadditions","volume":"147","author":"Chang","year":"2025","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026081410081792300_cit35","doi-asserted-by":"publisher","first-page":"124","DOI":"10.1038\/s44160-024-00659-6","article-title":"Palladium-Catalysed [2\u03c3+2\u03c0] Cycloaddition\nReactions of Bicyclo[1.1.0]butanes with Aldehydes","volume":"4","author":"Qin","year":"2025","journal-title":"Nat. Synth."},{"key":"2026081410081792300_cit36","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202513913","article-title":"Umpolung\nActivation of Bicyclobutanes via N-Heterocyclic Carbene Catalysis","volume":"137","author":"Chang","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081410081792300_cit37","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202507590","article-title":"Catalytic Activation of Acceptor-Acceptor\nBicyclobutanes Enabled by Lewis Base Catalysis","volume":"64","author":"Zhou","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081410081792300_cit38","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202314700","article-title":"Synthesis of 2-Azanorbornanes\nvia Strain-Release Formal Cycloadditions Initiated by Energy Transfer","volume":"62","author":"Chang","year":"2023","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081410081792300_cit39","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202512018","article-title":"SmI2-Catalyzed\nCoupling of Alkyl Housane Ketones and Alkenes in an Approach to Norbornanes","volume":"64","author":"Roy","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081410081792300_cit40","doi-asserted-by":"publisher","first-page":"12693","DOI":"10.1021\/acs.joc.5c01474","article-title":"Synthesis of Bicyclo[2.2.1]Heptanes\nvia Pyridine-Boronyl Radical-Catalyzed [2\u03c0 + 2\u03c3] Cycloaddition","volume":"90","author":"Perveen","year":"2025","journal-title":"J. Org. Chem."},{"key":"2026081410081792300_cit41","doi-asserted-by":"publisher","first-page":"7190","DOI":"10.1039\/C8CS00054A","article-title":"Energy Transfer\nCatalysis Mediated by Visible Light: Principles, Applications, Directions","volume":"47","author":"Strieth-Kalthoff","year":"2018","journal-title":"Chem. Soc. Rev."},{"key":"2026081410081792300_cit42","doi-asserted-by":"publisher","first-page":"13582","DOI":"10.1039\/D2SC04789F","article-title":"Synthesis of complex bicyclic scaffolds\nby intermolecular photosensitized dearomative cycloadditions of activated\nalkenes and naphthalenes","volume":"13","author":"Wang","year":"2022","journal-title":"Chem. Sci."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.6c02514","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/32\/10231\/66370341\/acs.orglett.6c02514.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/32\/10231\/66370341\/acs.orglett.6c02514.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T14:20:26Z","timestamp":1786717226000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/orlef7\/article\/28\/32\/10231\/5240835\/Synthesis-of-Norbornanes-via-Photosensitized"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,3]]},"references-count":42,"journal-issue":{"issue":"32","published-online":{"date-parts":[[2026,8,3]]},"published-print":{"date-parts":[[2026,8,14]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.6c02514","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,3]]}}}