Novel reaction pathways for 2-pyridone [4+4] photoadducts |
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Authors: | Chen Peiling Chen Yanping Carroll Patrick J Sieburth Scott McN |
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Institution: | Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19010, USA. |
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Abstract: | Structure: see text] Transannular ring closure of a pyridone-furan 4+4] photoadduct has been evaluated in a model system. A combination of nitrogen substitution and an isopropyl group gave full control of the four new stereogenic centers. Chlorination transformed the 1,5-cyclooctadiene to a 4.2.0] ring system instead of to the expected 3.3.0] ring system. Changing an alkene to an enone suppressed this pathway and led to a new rearrangement, converting the 5-8-5 ring system to a 6-7-5 system. |
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