The preparation of bicylic lactam 2 is described, employing an acetoacetate-based synthesis of 1,4-ketoacid 3. The lactam 2 was shown to undergo a thermal ene reaction at 280-300 degrees C to afford tricycle 7. Reduction of the ene product followed by removal of the chiral auxiliary fragment provided the unusual lactam system 9 in highly enantioenriched form.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2736314 | PMC |
| http://dx.doi.org/10.1021/jo801696r | DOI Listing |
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