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In this study, we demonstrate a sustainable approach to design an overcrowded alkene and an\n                    <jats:italic>O<\/jats:italic>\n                    \u2010heterocyclic phenanthrene derivative using a bio\u2010based enantiopure flavanone,\n                    <jats:italic>(\u2010)<\/jats:italic>\n                    \u2010isolonchocarpin, as starting material. The synthesis involves a McMurry deoxygenative homocoupling reaction to generate a sterically hindered overcrowded alkene, which can further undergo photochemical\n                    <jats:italic>(E<\/jats:italic>\n                    \/\n                    <jats:italic>Z)<\/jats:italic>\n                    \u2010isomerization and oxidative 6\u03c0\u2010electrocyclization. The oxidation product was shown to have emission properties, highlighting the potential of synthesizing bio\u2010based chromophoric compounds in minimal steps. Computational studies using spin\u2010flip time\u2010dependent density functional theory (SF\u2010TDDFT) reveal that the inherent chirality of the starting material induces asymmetry in the rotational pathway, biasing the directionality of motion. By integrating enantiopure natural products into functional photoresponsive materials, this work offers a more sustainable route to develop new bio\u2010based photoresponsive molecular machines while deepening our understanding of chirality\u2010driven motion in dynamic systems.\n                  <\/jats:p>","DOI":"10.1002\/chem.71180","type":"journal-article","created":{"date-parts":[[2026,5,30]],"date-time":"2026-05-30T05:41:08Z","timestamp":1780119668000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["A Bio\u2010Based Chiroptical Overcrowded Alkene From Flavanone: Photoreactivity and Theoretical Investigation"],"prefix":"10.1002","volume":"32","author":[{"given":"Deryl H.","family":"Limawan","sequence":"first","affiliation":[{"name":"Organic Chemistry Division, Department of Chemistry, Faculty of Mathematics and Natural Sciences Institut Teknologi Bandung  Bandung Indonesia"},{"name":"Stratingh Institute for 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