Oxa-di-pi-methane photochemical rearrangement of quinuclidinones. Synthesis of pyrrolizidinones |
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| Authors: | McClure Cynthia K Kiessling Anthony J Link Jeffrey S |
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| Affiliation: | Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA. cmcclure@chemistry.montana.edu |
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| Abstract: | [reaction: see text] The oxa-di-pi-methane (ODPM) photochemical rearrangement, a triplet-sensitized sigmatropic 1,2-acyl shift of beta,gamma-enones, was successful utilizing methyl and heptyl 1-aza-3-carboalkoxybicyclo[2.2.2]oct-2-en-5-ones (quinuclidinones) as the photoprecursors. The cyclopropane of the heptyl ester tricyclic photoproduct could be opened with lithium dimethylcuprate or via hydrogenolysis to produce the corresponding pyrrolizidinone skeletons. |
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