P-64 抗菌活性物質6-Tuliposide Bの合成(ポスター発表の部)

概要

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6-Tuliposide B, a secondary metabolite of tulip cultivars was recently revealed to have antimicrobial activity and be specifically distributed in anthers. These observations suggest that the production of 6-tuliposide B is a novel defense strategy in tulips to protect pollens from bacterial pollution1. To investigate the molecular property and biological activity of this natural product, we undertook total synthesis of 6-tuliposide B (1) using Baylis-Hillman (BH) reaction as a key step. 6-Tuliposide B was synthesized via BH reaction of tert-butyldimethylsilyloxy-acetaldehyde (2) and D-glucose-derived sugaracrylate (10c), followed by TFA treatment. In BH reaction, triethylsilyl-protected sugaracrylate (3) provided no BH adduct even after 20 days probably because of its low affinity with catalyst. On the other hand, sugaracrylate (10c) with free hydroxyl group afforded a BH adduct (13c) after 40 hours in 32 % yield with 44 %d.e.. It was considered that remote asymmetric induction in this reaction was originated from interaction between catalyst and chiral sugar moiety having free hydroxy group.
天然有機化合物討論会の論文
2007-08-24