Mimicking the Main Events of the Biosynthesis of Drimentines: Synthesis of Δ8′-Isodrimentine A and Related Compounds

التفاصيل البيبلوغرافية
العنوان: Mimicking the Main Events of the Biosynthesis of Drimentines: Synthesis of Δ8′-Isodrimentine A and Related Compounds
المؤلفون: Erwan Poupon, Mehdi A. Beniddir, Adam Skiredj, Laurent Evanno
المصدر: European Journal of Organic Chemistry. 2016:2954-2958
بيانات النشر: Wiley, 2016.
سنة النشر: 2016
مصطلحات موضوعية: Indole test, 010405 organic chemistry, Chemistry, Stereochemistry, Organic Chemistry, Sequence (biology), 010402 general chemistry, Sesquiterpene, 01 natural sciences, In vitro, 0104 chemical sciences, Human tumor, chemistry.chemical_compound, Biosynthesis, Biomimetic synthesis, Intramolecular force, Physical and Theoretical Chemistry
الوصف: Drimentines are a family of tetracyclic alkaloids biosynthetically originating from the condensation of sesquiterpene units onto cyclic dipeptides. A straightforward assembly of the fused “pyrroloindoline–diketopiperazine” core of drimentines is described herein and used for the synthesis of Δ8′-isodrimentine A. The strategy involves a bio-inspired indole dearomatization of a tryptophan-containing cyclodipeptide by a drimane-type decaline followed by the intramolecular trapping of the resulting indolenine intermediate in an uninterrupted reactive sequence. The starting diketopiperazine was prepared by classical peptidic coupling and the drimane-type decaline from (+)-sclareolide. A fully biomimetic approach with a linear sesquiterpene unit is also reported and led to farnesylated pyrroloindoline–diketopiperazines, which correspond to the proposed biosynthetic precursors of both drimentines A and D. The end product Δ8′-isodrimentine A and its congeners were evaluated in vitro for their cytotoxic activities against three human tumor cell lines.
تدمد: 1434-193X
URL الوصول: https://explore.openaire.eu/search/publication?articleId=doi_________::430285cedb91ea06693668324510649c
https://doi.org/10.1002/ejoc.201600444
حقوق: CLOSED
رقم الأكسشن: edsair.doi...........430285cedb91ea06693668324510649c
قاعدة البيانات: OpenAIRE