P-52 Pamamycinをモデルとしたマクロライド型新規イオノフォアの合成研究(ポスター発表の部)

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In the investigation of an aerial mycelium-inducing substance of Streptomyces alboniger, pamamycin-607 (1) was found to be an active principle in 1988 and its derivatives were also characterized at that time as shown Fig. 1. These compounds belong to the macrolide family and have a unique structure in which the side chain with dimethyl amino group covered the macrolactone ring. Here we describe the synthetic studies of a novel ionophore by the use of the steric character of pamamycins. 1. Synthesis of macrolides from homononactic acid derivatives Homononactic acid, a basic component of tetranactin which has a potent K^+ ionophore, was used a construction of macrolide compounds with a modified Yamaguchi's macrolactonization and Mitsunobu reaction. Consequently, 18 macrolides with a different ring size and different stereochemistry were yielded. 2. Character of macrolide as an ionophore All of synthetic macrolides was checked up an efficacy of ionophore; 1) alkali metal picrate extraction experiments, 2) competitive cation transport experiments, and 3) FAB-MS binding experiments. 3. Introduction of side chain to homononactic acid derivatives We investigated the regio- and stereoselective introduction of side chain to 8 and 14 by aldol reaction and alkylation.
天然有機化合物討論会の論文
1994-09-20