1464809-12-8Relevant academic research and scientific papers
Combination of Pseudo-Natural Product Design and Formal Natural Product Ring Distortion Yields Stereochemically and Biologically Diverse Pseudo-Sesquiterpenoid Alkaloids
Liu, Jie,Flegel, Jana,Otte, Felix,Pahl, Axel,Sievers, Sonja,Strohmann, Carsten,Waldmann, Herbert
, p. 21384 - 21395 (2021)
We describe the synthesis and biological evaluation of a new natural product-inspired compound class obtained by combining the conceptually complementary pseudo-natural product (pseudo-NP) design strategy and a formal adaptation of the complexity-to-diversity ring distortion approach. Fragment-sized α-methylene-sesquiterpene lactones, whose scaffolds can formally be viewed as related to each other or are obtained by ring distortion, were combined with alkaloid-derived pyrrolidine fragments by means of highly selective stereocomplementary 1,3-dipolar cycloaddition reactions. The resulting pseudo-sesquiterpenoid alkaloids were found to be both chemically and biologically diverse, and their biological performance distinctly depends on both the structure of the sesquiterpene lactone-derived scaffolds and the stereochemistry of the pyrrolidine fragment. Biological investigation of the compound collection led to the discovery of a novel chemotype inhibiting Hedgehog-dependent osteoblast differentiation.
Exo-Selective construction of spiro-[butyrolactone-pyrrolidine] via 1,3-dipolar cycloaddition of azomethine ylides with α-methylene-γ- butyrolactone catalyzed by Cu(I)/DTBM-BIPHEP
Li, Qing-Hua,Liu, Tang-Lin,Wei, Liang,Zhou, Xiang,Tao, Hai-Yan,Wang, Chun-Jiang
, p. 9642 - 9644 (2013/10/08)
An expedient access to optically active spiro-[butyrolactone-pyrrolidine] was successfully developed via an unprecedented Cu(i)-catalyzed exo-selective 1,3-DC of azomethine ylides with α-methylene-γ-butyrolactone, which exhibited high diastereoselectivity (>98:2), excellent enantioselectivity (96->99% ee) and a broad substrate scope under mild conditions. The Royal Society of Chemistry 2013.
