114(P50) 酵素化学的手法を基盤とするNikkomycin Bの合成(ポスター発表の部)
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Nikkomycins are peptidyl nucleoside antibiotics which have been isolated from the culture broths of Streptomyces tendae and Streptomyces cacaoi subsp. asoensis. These antibiotics are potent competitive inhibitors of chitin synthetase and exhibit antifungal, insecticidal and acaricidal activities. The total synthesis of nikkomycin B has already been achieved by the coupling of two structural units, the N-terminal amino acid 1 and the C-terminal nucleoside amino acid, uracil polyoxin C. We now report a stereoselective synthesis of Barrett's intermediate (2S,3S,4S)-1 based on the chemo-enzymatic method and its application to the formal total synthesis of nikkomycin B by the coupling of uracil polyoxin C congener 30. Diastereoselective reduction of (±)-6 with n-Bu_4NBH_4^3 gave the (±)-anti-4 (71.3%) along with a small amount of the (±)-syn-5 (4.8%) with high anti-diastereoselectivity (anti/syn =15/1). Successive conversion of (±)-anti-4 into mono acetate (±)-8 followed by asymmetric hydrolysis by a lipase "Amano P" from Pseudomonas sp. gave an optically pure (2S,3S)-8, which was converted into the synthetic intermediate (2S,3S,4S)-1 for the synthesis of nikkomycin B. On the other hand, uracil polyoxin C congener 30, corresponding to the C-terminal nucleoside amino acid part of nikkomycin B was synthesized from the reported 1-(methyl 2',3'-di-O-acetyl-5'-azido-5'-deoxy-β-D-allofuranosyluronate)uracil 27. The coupling reaction of uracil polyoxin C congener 30 with the (2S,3S,4S)-1 gave an important Barrett's intermediate 31 for the synthesis of nikkomycin B.
- 天然有機化合物討論会の論文
- 1998-08-31
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