Total synthesis and biological evaluation of Amaryllidaceae alkaloids: Narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives

Tomas Hudlicky*, Uwe Rinner, David Gonzalez, Hulya Akgun, Stefan Schilling, Peter Siengalewicz, Theodore A. Martinot, George R. Pettit

*المؤلف المقابل لهذا العمل

نتاج البحث: المساهمة في مجلةArticleمراجعة النظراء

188 اقتباسات (Scopus)

ملخص

Biocatalytic approaches have yielded efficient total syntheses of the major Amaryllidaceae alkaloids, all based on the key enzymatic dioxygenation of suitable aromatic precursors. This paper discusses the logic of general synthetic design for lycoricidine, narciclasine, pancratistatin, and 7-deoxypancratistatin. Experimental details are provided for the recently accomplished syntheses of narciclasine, ent-7-deoxypancratistatin, and 10b-epi-deoxypancratistatin via a new and selective opening of a cyclic sulfate over aziridines followed by aza-Payne rearrangement. The structural core of 7-deoxypancratistatin has also been degraded to a series of intermediates in which the amino inositol unit is cleaved and deoxygenated in a homologous fashion. These truncated derivatives and the compounds from the synthesis of the unnatural derivatives have been tested against six important human cancer cell lines in an effort to further develop the understanding of the mode of action for the most active congener in this group, pancratistatin. The results of the biological activity testing as well as experimental, spectral, and analytical data are provided in this manuscript for all relevant compounds.

اللغة الأصليةEnglish
الصفحات (من إلى)8726-8743
عدد الصفحات18
دوريةJournal of Organic Chemistry
مستوى الصوت67
رقم الإصدار25
المعرِّفات الرقمية للأشياء
حالة النشرPublished - ديسمبر 13 2002
منشور خارجيًانعم

ASJC Scopus subject areas

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بصمة

أدرس بدقة موضوعات البحث “Total synthesis and biological evaluation of Amaryllidaceae alkaloids: Narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives'. فهما يشكلان معًا بصمة فريدة.

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