Preparation of cruciferous phytoalexin related metabolites, (−)-dioxibrassinin and (−)-3-cyanomethyl-3-hydroxyoxindole, and determination of their absolute configurations by vibrational circular dichroism (VCD)

✍ Scribed by Kenji Monde; Tohru Taniguchi; Nobuaki Miura; Shin-Ichiro Nishimura; Nobuyuki Harada; Rina K Dukor; Laurence A Nafie

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 161 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)01513-2

✦ Synopsis

Cruciferous phytoalexin related metabolites, (-)-dioxibrassinin ( ) and (-)-3-cyanomethyl-3-hydroxyoxindole (2) were prepared from isatin as racemates and were resolved by chiral HPLC. Their absolute configurations were determined by the new chiroptical technique, vibrational circular dichroism (VCD), as well as by the conventional electronic circular dichroism (ECD). It is concluded that the absolute configurations of the naturally occurring (-)-1 and (-)-2 are both S.