Journal ArticleDOI
Total syntheses of furaquinocin A, B, and E
TLDR
A modular approach to the total synthesis of fURAquinocins culminated in the total syntheses of furaquinocin A, B, and E.Abstract:
A modular approach to the total synthesis of furaquinocins culminated in the total syntheses of furaquinocin A, B, and E. A Pd-catalyzed dynamic kinetic asymmetric transformation (DYKAT) on carbonates derived from Baylis-Hillman adducts, followed by a reductive Heck cyclization allows the enantio- and diastereoselective construction of dihydrobenzofuran 32. Introduction of a double unsatured side chain via Horner-Wadsworth-Emmons reaction and assembly of the naphthoquinone with squaric acid based methodology leads to furaquinocin E. The use of differentially substituted squaric acid derivatives allows the synthesis of three analogues of furaquinocin E. The additional stereocenters in furaquinocin A and B can be introduced with a diastereoselective Sakurai allylation. The stereoselective elongation of the side chain is possible using cross metathesis or ring closing metathesis. The obtained late-stage intermediates were successfully transformed to furaquinocin A and B.read more
Citations
More filters
Journal ArticleDOI
Advances in the Baylis–Hillman reaction-assisted synthesis of cyclic frameworks
Vijay Singh,Sanjay Batra +1 more
TL;DR: A review of cyclic compounds from the Baylis-Hillman chemistry covering the literature from 2003 to 2007 can be found in this article, where several reaction strategies leading to these cyclic frameworks are delineated in the figure.
Journal ArticleDOI
Cupreines and Cupreidines: An Emerging Class of Bifunctional Cinchona Organocatalysts
TL;DR: Recently, new cinchona catalysts have been developed that feature a phenolic OH group in the C6' position, a structural feature that allows a diverse set of reactions to be catalyzed in a highly stereoselective fashion as discussed by the authors.
Journal ArticleDOI
Catalytic asymmetric allylic alkylation employing heteroatom nucleophiles: a powerful method for C–X bond formation
TL;DR: The use of heteroatom-centered nucleophiles in this reaction is a powerful method for asymmetric C-X (X = heteroatoms) bond formation as discussed by the authors. But this method is not suitable for the use of metal catalyzed asymmetric allylic alkylation.
Journal ArticleDOI
Pd2(dba)3 as a Precursor of Soluble Metal Complexes and Nanoparticles: Determination of Palladium Active Species for Catalysis and Synthesis
TL;DR: In this paper, the authors developed a convenient NMR procedure to reveal the nature of Tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) and to determine the purity of the complex.
References
More filters
Journal ArticleDOI
Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.
TL;DR: These air- and water-tolerant complexes were shown to exhibit an increased ring-closing metathesis activity at elevated temperature when compared to that of the parent complex 2 and the previously developed complex 3.
Journal ArticleDOI
Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity
TL;DR: The identity of Alamar Blue is shown as resazurin, a very simple and versatile way of measuring cell proliferation and cytotoxicity that presents numerous advantages over other cytot toxicity or proliferation tests but there are several drawbacks to the routine use.
Journal ArticleDOI
Olefin Metathesis and Beyond
TL;DR: In this paper, the authors provide an overview of the development of catalysts for olefin metathesis which combine high activity, durability, and excellent tolerance towards polar functional groups.
Journal ArticleDOI
Recent Advances in the Baylis−Hillman Reaction and Applications
Journal ArticleDOI
Synthesis of Functionalized Olefins by Cross and Ring-Closing Metatheses
TL;DR: In this paper, a single-step synthesis of α-functionalized olefins by intermolecular cross-metathesis and intramolecular ring-closing metathesis using ruthenium alkylidene 3 was reported.