73 非環状アミドアルカロイドならびに大環状ラクタムアルカロイドの新合成研究

概要

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An efficiently monitored aminolysis of 3-acylthiazolidine-2-thione (1) has been found to give a very high yield of amide (6). Experimental results are shown in Table 2. The similar aminolysis of 3-hexadecanoylthiazolidine-2-thione (1c) with many kinds of aminoalcohols resulted in the chemospecific formation of the desired hydroxyamides in satisfactory yields. (See Table 3.) Subsequently, naturally occurring amide alkaloids, fagaramide (14), dolichotheline (16), and maytenine (18) were synthesized in good yields by the application of the foregoing aminolysis. Synthesis of macrocyclic lactams was also successfully carried out. (See Table 4.) The total synthesis of codonocarpine (37), a macrocyclic spermidine alkaloid,utilizing this aminolysis as a key step is now in progress.
天然有機化合物討論会の論文
1979-09-20