The asymmetric synthesis of tetraol (+)-3, a degradation product derived from a C2 symmetric oxasqualenoid intricatetraol 1, has been achieved through the two-directional synthesis starting from diol 7, realizing the further additional assignment of the incomplete stereostructure of 1, the stereochemistry of which is difficult to determine otherwise.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/b608098g | DOI Listing |
Angew Chem Int Ed Engl
April 2023
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, 100084, China.
Herein we report a two-directional cyclization strategy for the synthesis of highly strained depth-expanded oxygen-doped chiral molecular belts of the zigzag-type. From the easily accessible resorcin[4]arenes, an unprecedented cyclization cascade generating fused 2,3-dihydro-1H-phenalenes has been developed to access expanded molecular belts. Stitching up the fjords through intramolecular nucleophilic aromatic substitution and ring-closing olefin metathesis reactions furnished a highly strained O-doped C -symmetric belt.
View Article and Find Full Text PDFJACS Au
January 2023
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.
Herein, we describe the development of a new strategy for the synthesis of unsaturated oligoesters sequential metal- and reagent-free insertion of vinyl sulfoxonium ylides into the O-H bond of carboxylic acid. Like two directional coupling of amino acids (N- to C-terminal and C- to N-terminal) in peptide synthesis, the present approach offers a strategy in both directions to synthesize oligoesters. The sequential addition of the vinyl sulfoxonium ylide to the carboxylic acids (acid iteration sequence) in one direction and the sequential addition of the carboxylic acids to the vinyl sulfoxonium ylide (ylide iteration sequence) in another direction yield (Z)-configured unsaturated oligoesters.
View Article and Find Full Text PDFChem Sci
August 2022
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Huazhong University of Science and Technology 13 Hangkong Road Wuhan Hubei 430030 China
Herein, we report a novel fluorous-tag assisted two-directional oligosaccharide assembly strategy, which maintained the high coupling efficiency of solution-phase synthesis and featured the advantage of an easy purification process comparable to solid-phase synthesis. A well-designed fluorous tag was decorated on the latent anomeric leaving group in interrupted Pummerer reaction mediated (IPRm) glycosylation. The high efficiency of the in-solution phase glycosylation and the unique affinity of the fluorous tag towards polytetrafluoroethylene (PTFE) particles allowed flexible assembly from the reducing end to the non-reducing end and fast purification by PTFE-assisted filtration.
View Article and Find Full Text PDFOrg Lett
July 2022
Department of Chemistry, Memorial University of Newfoundland, 45 Arctic Avenue, St. John's, NL Canada, A1C 5S7.
Two-directional contractive annulation of [2.2]paracyclophane has led to the synthesis of -[1](1,6)naphthaleno[1](1,6)naphthalenophane (). This [1.
View Article and Find Full Text PDFBioconjug Chem
April 2022
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Zhang Jiang Hi-Tech Park, Pudong, Shanghai, 201203, P. R. China.
Macrocyclic peptides are an important class of therapeutic agents for the biological targets that are difficult to modulate by small-molecule compounds. Meanwhile, DNA-encoded library technology (DELT) provides a powerful platform for hits discovery. The unity of both fields has proven highly productive in finding cyclic peptide hits against diverse pharmaceutical proteins.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!