17 殺ダニ物質グアラマイシンの全合成(口頭発表の部)

概要

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Gualamycin is a novel water-soluble acaricide isolated from the culture broth of Streptomyces sp. NK11687 in 1995. The structure was deduced to be 1 mainly from the spectral and/or X-ray crystallographic analysis of its disaccharide and aglycone portions (2 and 3). The absolute structure of the disaccharide, however, remained undetermined. We now report the isolation and the first total synthesis of gualamycin to confirm the absolute structure 1. The disaccharide 2 was synthesized from properly protected D-gulosamine and D-galactose derivatives. The aglycone unit 3 was synthesized from t-butyldimethylsilyl 2-azido-2-deoxy-α-L-mannopyranoside 8 through the dihydroxylation of the olefin 11 and S_N2-type cyclization of 15. These syntheses confirmed the absolute structures of both segments. Finally, both segments were combined by reaction of the thioglycoside of the disaccharide 22 with the benzylidenated aglycone 21 to give, after deprotection, gualamycin (1), which is identical with the natural acaricide in all respects.
天然有機化合物討論会の論文
1995-09-01