Synthesis, absolute configuration, and enantiomeric enrichment of a cruciferous oxindole phytoalexin,(S)-(-)-spirobrassinin, and its oxazoline analog

…, P Kutschy, K Monde, H Goto, N Harada…

文献索引：Suchy; Kutschy; Monde; Goto; Harada; Takasugi; Dzurilla; Balentova Journal of Organic Chemistry, 2001 , vol. 66, # 11 p. 3940 - 3947

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被引用次数: 134

摘要

Stereochemical studies of a cruciferous oxindole phytoalexin,(S)-(-)-spirobrassinin [(-)-4], and its oxazoline analogue, spirooxazoline (11), were carried out. Racemic spirobrassinin [(±)-4] was synthesized by SOCl2-or MsCl-mediated cyclization of dioxibrassinin [(±)-8]. Treatment of (3-hydroxyoxindol-3-yl) methylammonium chloride [(±)-9] with CSCl2 and subsequent methylation of the obtained spirooxazolidinethione (±)-10 afforded ...