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- Title
Mimicking the Main Events of the Biosynthesis of Drimentines: Synthesis of Δ8′-Isodrimentine A and Related Compounds.
- Authors
Skiredj, Adam; Beniddir, Mehdi A.; Evanno, Laurent; Poupon, Erwan
- Abstract
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.
- Subjects
MIMICRY (Chemistry); BIOSYNTHESIS; CHEMICAL synthesis; ALKALOIDS; ALKALOID synthesis; ORGANIC chemistry research
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 17, p2954
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600444