[reaction: see text] The asymmetric synthesis of the methylated tryptophan portion of hemiasterlin peptides is described. The key reactions are a SnCl4-mediated ring opening of epoxynitriles or epoxysulfones by N-methylindole followed by an asymmetric Strecker reaction. A second approach involving opening of glycidic esters by indoles is also described.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol016982+ | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Enantioselective Catalytic Synthesis of Inherently Chiral Calixarenes.
Chem Rec
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing, 401331, P. R. China.
Since the introduction of the concept of inherent chirality by Böhmer, an important part of research focused on the asymmetric synthesis of calixarene macrocycles. However, long synthetic procedures and tedious separation strategies hampered the application of this technology in many topics of organic chemistry, including enantioselective molecular recognition and catalysis. Very recently, a new generation of enantioselective catalytic methodologies has been reported, able to provide highly functionalized, inherently chiral calixarenes in a straightforward manner.
View Article and Find Full Text PDFEnantioselective synthesis of 2-substituted bicyclo[1.1.1]pentanes via sequential asymmetric imine addition of bicyclo[1.1.0]butanes and skeletal editing.
Nat Chem
January 2025
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, China.
The substitution of an aromatic ring with a C(sp)-rich bicyclic hydrocarbon, known as bioisosteric replacement, plays a crucial role in modern drug discovery. Substituted bicyclo[1.1.
View Article and Find Full Text PDFEnantioselective Borylcupration/Cyclization of Alkene-Tethered Oxime Esters.
Angew Chem Int Ed Engl
January 2025
University of Toronto, Dept. of Chemistry, 80 St. George Street, M5S 3H6, Toronto, CANADA.
A copper-catalyzed enantioselective synthesis of borylated 1-pyrrolines from γ,δ-unsaturated oxime esters is reported. Twenty-four novel 1-pyrroline derivatives are reported in yields ranging from 26% to 96% and enantioselectivities from 74.5:25.
View Article and Find Full Text PDFMAdPHOS, a P-Stereogenic Aminodiphosphane Ligand with Adamantyl Groups: Synthesis, NH/PH Tautomerism, and Rhodium and Nickel Complexes.
J Org Chem
January 2025
Institute for Research in Biomedicine (IRB Barcelona). The Barcelona Institute of Science and Technology (BIST), Baldiri Reixach 10, 08028 Barcelona, Spain.
A novel chiral ligand, named MAdPHOS, bearing a P-stereogenic phosphane and a diadamantyl phosphane linked by a NH bridge has been synthesized. This bulky, C-symmetric, PNP ligand has been prepared from enantiopure -butylmethyl aminophosphane and was obtained as a crystalline solid. The NH/PH tautomerism, air-stability, and σ-donor capacity of MAdPHOS have been assessed herein.
View Article and Find Full Text PDFSymmetry Breaking: Case Studies with Organic Cage-Racemates.
Acc Chem Res
January 2025
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China.
ConspectusSymmetry is a pervasive phenomenon spanning diverse fields, from art and architecture to mathematics and science. In the scientific realms, symmetry reveals fundamental laws, while symmetry breaking─the collapse of certain symmetry─is the underlying cause of phenomena. Research on symmetry and symmetry breaking consistently provides valuable insights across disciplines, from parity violation in physics to the origin of homochirality in biology.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!