14 抗生物質合成に有用な新しい高選択的不斉誘導

概要

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The most interesting targets for synthetic chemists have been focused on the biologically active natural products such as macrolide, macrolactam, polyether, and β-lactam antibiotics. These compounds have complicated chemical structures possessing several asymmetric carbon atoms. Usually, only one enantiomer exhibits the desirable activity. Therefore, optically active, simple acyclic compounds have been utilized as the starting materials in their total syntheses. Use of a symmetrical molecule is one of the important strategies in the asymmetric synthesis, because it may be a benefitable precursor for an enantio-convertible chiral compound by utilizing its own bifunctionality. We have designed and developed a novel, nonenzymatic procedure: a highly selective asymmetric induction into a symmetrical, acyclic molecule such as 3-methylglutaric acid (6) or meso-2,4-dimethylglutaric acid (22) via an aminolysis of 4(R)-MCTT diamide 7 or 25, respectively. This new chemical asymmetric synthesis is not only useful as a practical synthetic tool for the synthesis of antibiotics but also as an aid in the elucidation of the action of enzymes such as α-chymotrypsin and pig liver esterase.
天然有機化合物討論会の論文
1982-09-10