6 分子内配糖化を鍵反応とする抗ダニ抗生物質AB3217-Aの合成研究(口頭発表の部)

概要

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A novel antibiotic AB3217-A (1) was isolated in 1992 from the fermentation broth of Streptomyces platensis AB3217. It exhibits anti-mite, antimicrobial, and herbicidal activities. The unique structure of 1 was elucidated by spectroscopic means and its absolute configuration was established by X-ray crystallographic analysis. We now report the synthetic studies of AB3217-A. AB3217-A was divided into two portions, namely the deacetylanisomycin segment A and the β-D-xylofuranose segment B. The epoxide 3, which was prepared from dimethyl L-tartrate (2) according to the known procedure, was transformed to pyrrolidine-aldehyde 10 by cyclization of aminoepoxide in the presence of Lewis acid as a key step. This aldehyde 10 was subjected to the stereoselective anisylation followed by successive oxidation and stereoselective reduction to afford the desired deacetylanisomycin segment 14. α-Phenylthioglycoside 20, corresponding to the β-D-xylofuranose segment, was prepared from diacetone-D-glucose (15) by a conventional procedure. The coupling of deacetylanisomycin segment 14 and β-D-xylofuranose segment 20 was realized by treatment with NaN(TMS)_2 in DMF to afford the coupling product 21, which was subjected to cyclization using NBS to give the 9-membered ring product 23. We are now investigating deprotection of 23 to accomplish the total synthesis of AB3217-A.
天然有機化合物討論会の論文
1993-09-10