Reoptimization of the Organocatalyzed Double Aldol Domino Process to a Key Enal Intermediate and Its Application to the Total Synthesis of Δ12-Prostaglandin J3
作者： Andrejs Pelšs , Narasimhulu Gandhamsetty , James R. Smith , Damien Mailhol , Mattia Silvi
关键词: Chemistry 、 Organocatalysis 、 Total synthesis 、 Combinatorial chemistry 、 Stereoselectivity 、 Prostaglandin 、 Succinaldehyde 、 Yield (chemistry) 、 Aldol reaction 、 Bicyclic molecule
摘要: Re-investigation of the l-proline catalyzed double aldol cascade dimerization succinaldehyde for synthesis a key bicyclic enal intermediate, pertinent in field stereoselective prostaglandin synthesis, is reported. The yield this process has been more than doubled, from 14 % to 29 isolated on multi-gram scale (32 NMR yield), through conducting detailed study reaction solvent, temperature, and concentration, as well catalyst screen. synthetic utility intermediate further demonstrated total Δ12 -prostaglandin J3 , compound with known anti-leukemic properties.
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