65 ビラントマイシンの全合成と立体化学(ポスター発表の部)

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The unusual metabolite virantmycin(1), isolated from the fermentation broth of Streptomyces nitrosporeus, is strongly expected as a lead compound of antiviral chemotherapeutic agents because of its antifungal and potent inhibitory activity against various RNA and DNA viruses. The antiviral antibiotic having tetrahydroquinoline skelton such as 1 is very rare. We have developed two synthetic methods of 1 and the syntheses have been achieved in each of racemic and optically active form. Through the present syntheses, the veiled stereochemistry at the two chiral centers of 1 has been unambiguously assigned to 2R, 3R. The syntheses of (±)-1 and (±)-2 were carried out through the stereospecific route employing intramolecular nitrene-addition reaction as a key step (10→14, 11→15). NOE experiments with cyclic carbamates 18 and 19, which possessed conformationally rigid piperidine ring system, revealed the relative configuration of (±)-1 and its diastereomer (±)-2. Thus, the configuration of natural product was established as shown in 1. The optically active synthesis of (+)-1 was set out from allyl alcohol 20 which was subjected to the asymmetric epoxidation to afford optically active epoxy alcohol 21. The application of the exiton chirality method to 4-dimetyl-aminobenzoate derivative 26 derived from alcohol 25 confirmed the absolute configuration at C-3 position of 25. Thus, through the total synthesis of (+)-1, the absolute configuration of natural product was clearly determined to be 2R, 3R.
天然有機化合物討論会の論文
1990-09-25

65 ビラントマイシンの全合成と立体化学(ポスター発表の部)

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