Highly efficient total synthesis of Δ-PGJ2, 15-deoxy-Δ-PGJ2, and their analogues |
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Authors: | Hukum P. Acharya |
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Affiliation: | Department of Biomolecular Engineering, Tokyo Institute of Technology B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan |
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Abstract: | Palladium-catalyzed reaction of TBS ether of 4-cyclopentene-1,3-diol monoacetate (>95% ee) with an anion derived from methyl malonate and a base such as t-BuOK and LDA proceeded highly efficiently and reproducibly. The product obtained in >90% isolated yield was transformed in five steps into the key cyclopentenone possessing the α-chain at the γ position. Aldol reaction of this enone with the ω-chain aldehyde afforded the aldol adduct, and exposure of the derived mesylate to Al2O3 furnished the cross-conjugated dienone of the full structure. Finally, functional group manipulation furnished Δ12-PGJ2 efficiently. Similarly, 15-deoxy-Δ12,14-PGJ2, 5,6-acetylene analogues, and a 5,6-dihydro analogue were synthesized. |
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Keywords: | Aldol reaction Cyclopentenone Palladium PPARγ Δ12-PGJ2 15-Deoxy-Δ12,14-PGJ2 |
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