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Synthesis 1973; 1973(7): 397-412
DOI: 10.1055/s-1973-22222
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Methods for the Synthesis of 3-Oxocyclopentenes

Robert A. ELLISON*
  • *School of Pharmacy, University of Wisconsin, Madison, Wisconsin 53706, U. S. A.
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Publication Date:
12 September 2002 (online)

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The numerous methods for the preparation of the title compounds are surveyed. These compounds are major synthons for several important natural products including cis-jasmone, rethrolones, and prostaglandins. Basic approaches include cyclization of 1,4-diketones, modification of dioxocyclopentanes, molecular rearrangements, and direct introduction of oxygen. 1. Routes Based on 1,4-diketones 1.1. ß-Ketoester and Related Condensations 1.2. Approaches by way of Furans 1.3. Other 1,4-Diketone Preparations 2. Routes Based on Dioxocyclopentanes 2.1. 1,3-Dioxocyclopentanes 2.2. 1,2-Dioxocyclopentanes 3. Routes Based on Molecular Rearrangement 4. Direct Introduction of Oxygen 5. Miscellaneous Routes 6. Conclusions