Tetrahedron p. 13347 - 13368 (1994)
Update date:2022-08-05
Topics:
Oikawa, Hideaki
Matsuda, Isamu
Kagawa, Takashi
Ichihara, Akitami
Kohmoto, Keisuke
AAL-toxins TA1 1 and TA2 2, host-specific toxins produced by Alternaria alternata, were degraded to 2-methylbutanol, 3-methylnonan-1,9-diol and N-protected 4-aminobutan-1,3-diol, which were further converted to (R)-MTPA esters. These esters were correlated with synthetic samples by comparison of their 500 MHz 1H-NMR spectra. The remaining stereocenters were determined by the comparison of 1H-NMR spectra of 6a and 7 derived from 1 and 2 with those of synthetic model compounds. These data conclude that AAL-toxins possess 2S, 4S, 5R, 11S, 13S, 14R and 15R configurations.
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Doi:10.1246/bcsj.69.1329
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