Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 38, Pages 9542-9545Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201802498
Keywords
aldol reaction; organocatalysis; prostaglandins; total synthesis; Delta(12)-PGJ(3)
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Funding
- EPSRC [EP/M012530/1, EP/G036764/1]
- Deutsche Forschungsgemeinschaft (DFG)
- Marie-Sklodowska-Curie Fellowship program [EC FP7 623426]
- [REGPOT-CT-2013-316149-InnovaBalt]
- BBSRC [BB/F011539/1] Funding Source: UKRI
- EPSRC [EP/M012530/1, EP/L011999/1, EP/K03927X/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K03927X/1] Funding Source: researchfish
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Re-investigation of the L-proline catalyzed double aldol cascade dimerization of succinaldehyde for the synthesis of a key bicyclic enal intermediate, pertinent in the field of stereoselective prostaglandin synthesis, is reported. The yield of this process has been more than doubled, from 14% to a 29% isolated yield on a multi-gram scale (32% NMR yield), through conducting a detailed study of the reaction solvent, temperature, and concentration, as well as a catalyst screen. The synthetic utility of this enal intermediate has been further demonstrated through the total synthesis of Delta(12)-prostaglandin J(3), a compound with known anti-leukemic properties.
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