Chemoenzymatic synthesis of amaryllidaceae constituents and biological evaluation of their C-1 analogues. the next generation synthesis of 7-deoxypancratistatin and trans -dihydrolycoricidine

Jonathan Collins, Uwe Rinner, Michael Moser, Tomas Hudlicky*, Ion Ghiviriga, Anntherese E. Romero, Alexander Kornienko, Dennis Ma, Carly Griffin, Siyaram Pandey

*المؤلف المقابل لهذا العمل

نتاج البحث: المساهمة في مجلةArticleمراجعة النظراء

58 اقتباسات (Scopus)

ملخص

An efficient synthesis of C-1 derivatives of 7-deoxypancratistatin is reported. The key steps include the following: selective opening of an epoxide with aluminum acetylide in the presence of an aziridine; solid-state silica-gel-catalyzed opening of an aziridine; and oxidative cleavage of a phenanthrene core and its recyclization to phenanthridone to provide the key C-1 aldehyde 22. The conversion of this aldehyde to C-1 acetoxymethyl and C-1 hydroxymethyl derivatives is described along with the evaluation of their biological activity against several cancer cell lines and in an apoptosis study. The C-1 acetoxymethyl derivative has shown promising activity comparable to that of the natural product. In addition, a total synthesis of trans-dihydrolycoricidine and a formal total synthesis of 7-deoxypancratistatin are reported from aldehyde 22. Detailed experimental and spectral data are provided for all new compounds.

اللغة الأصليةEnglish
الصفحات (من إلى)3069-3084
عدد الصفحات16
دوريةJournal of Organic Chemistry
مستوى الصوت75
رقم الإصدار9
المعرِّفات الرقمية للأشياء
حالة النشرPublished - مايو 7 2010
منشور خارجيًانعم

ASJC Scopus subject areas

  • ???subjectarea.asjc.1600.1605???

بصمة

أدرس بدقة موضوعات البحث “Chemoenzymatic synthesis of amaryllidaceae constituents and biological evaluation of their C-1 analogues. the next generation synthesis of 7-deoxypancratistatin and trans -dihydrolycoricidine'. فهما يشكلان معًا بصمة فريدة.

قم بذكر هذا