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The problem is further amplified when such an isomerization is integrated into cascade sequences, among which the regioselectivity and subsequent directionality are the major bottlenecks. Indeed, there are no reports till date for such a transformation. Herein, it is reported that such a controlled isomerization and subsequent cyclization cascade can be enabled by photosensitizer\u2010free direct irradiation of linearly conjugated acyclic polyenes in dichloromethane solvent using a 390\u2005nm LED. The directionality results from deconjugation of the extended \u03c0\u2010system in the transient <jats:italic>Z<\/jats:italic>\u2010isomer due to stabilizing n\u2192\u03c0* interactions between 1,4\u2010dicarbonyls (C=O\u2192C=O) or 1,4\u2010carbonyl\/\u2010aryl (C=O\u2192aryl) groups. The involvement of such noncovalent interactions has been supported by X\u2010ray crystallography and control experiments. Thus, conjugated trienones can be stereoselectively converted into oxabicyclo[3.2.1]octadienes in an atom\u2010 and step\u2010economic manner, including the first example by regioselective isomerization of a tetrasubstituted alkene. The reaction conditions are very general (&gt;46 examples). The reaction can be conducted under open air atmosphere at ambient temperature. Such a cascade cyclization can also be realized in solid state.<\/jats:p>","DOI":"10.1002\/chem.202300421","type":"journal-article","created":{"date-parts":[[2023,3,9]],"date-time":"2023-03-09T10:40:15Z","timestamp":1678358415000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Integrating Regioselective <i>E<\/i>\u2192<i>Z<\/i> Isomerization of Trienones with Cascade Sequences under Photosensitizer\u2010Free Direct Irradiation at 390\u2005nm"],"prefix":"10.1002","volume":"29","author":[{"given":"Rajib","family":"Maity","sequence":"first","affiliation":[{"name":"Organic and Medicinal Chemistry Division CSIR-Indian Institute of Chemical Biology  4, Raja S. C. 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