ملخص
(Chemical Equation Presented) Indole and several indoles functionalized at C-2 were condensed with oxiranes, vinyloxiranes, aziridines, and vinylaziridines in the solid state on the surface of silica. The yields of these reactions were compared to those obtained from Lewis acid-catalyzed ring-opening reactions performed in solution and found to be superior in each case. The solid-phase aziridine opening constituted a key step in the synthesis of the β-carbolin-1-one mimic of pancratistatin. Methyl 2-indolecarboxylate was found to react on the silica gel surface with N-tosylvinylaziridine in 68% yield. A nine-step synthesis of the pancratistatin mimic has been attained. The additional key transformation in this synthesis involved silica gel-catalyzed opening of an epoxide and hydrolysis of an acetonide. Detailed experimental procedures and full characterization are reported for all new compounds.
اللغة الأصلية | English |
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الصفحات (من إلى) | 3490-3499 |
عدد الصفحات | 10 |
دورية | Journal of Organic Chemistry |
مستوى الصوت | 70 |
رقم الإصدار | 9 |
المعرِّفات الرقمية للأشياء | |
حالة النشر | Published - أبريل 29 2005 |
منشور خارجيًا | نعم |
ASJC Scopus subject areas
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