A strategy for the synthesis of C-pseudodisaccharides that centers on the reaction of a C-linked crotyltin and a substituted pent-4-enal and a ring-closing metathesis-alkene dihydroxylation sequence on the derived crotylation products is illustrated in the preparation of analogues of the insulin modulatory inositol galactosamine-β-(1 → 4)-3-O-methyl-d- chiro-inositol (β-INS-2). The modularity of this approach and versatility of the pivotal crotylation products make this a potentially general methodology for diverse libraries of C-glycoinositols.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.8b00845 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Concise Synthesis of (-)-Veratramine and (-)-20--Veratramine via Aromative Diels-Alder Reaction.
J Am Chem Soc
January 2025
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
A concise and convergent synthesis of the isosteroidal alkaloids veratramine and 20--veratramine has been accomplished. A Horner-Wadsworth-Emmons olefination joins two chiral building blocks of approximately equal complexity and a transition-metal catalyzed intramolecular Diels-Alder cycloaddition-aromatization cascade constructs the tetrasubstituted arene. Other key steps include a highly diastereoselective crotylation of an -sulfonyl iminium ion and an Eschenmoser fragmentation.
View Article and Find Full Text PDFTotal Synthesis of (-)-Bipolarolide D.
JACS Au
November 2024
Department of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
(-)-Bipolarolide D is an ophiobolin-derived sesteterpenoid with a unique tetraquinane (5/5/5/5) tetracyclic skeleton decorated with a diverse set of functionalities. Herein we report a robust, scalable, and efficient total synthesis of this natural product in 1.8% overall yield.
View Article and Find Full Text PDFCopper-Catalyzed Regioselective and Enantioselective Hydropyridylation of Dienes for the Synthesis of Chiral Diaryl Compounds via Concerted Nucleophilic Aromatic Substitution.
Angew Chem Int Ed Engl
November 2024
Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141, Republic of Korea.
The synthesis of chiral 1,1-diaryl compounds, particularly those containing a pyridine moiety, is of significant interest due to their pharmaceutical applications. Here, we report the development of a copper-catalyzed enantioselective 1,4-hydropyridylation of conjugated dienes. Utilizing 2-fluoropyridine as the electrophile, CuOAc, and the chiral ligand Tol-BINAP, we optimized reaction conditions to achieve the desired chiral 1,1-diaryl products containing both a pyridine and a cis-crotyl group.
View Article and Find Full Text PDFSynthesis of alpha-Gal C-disaccharides.
Bioorg Med Chem
October 2024
Department of Chemistry, Hunter College and The Graduate Center of the City University of New York, New York, NY 10016, United States. Electronic address:
The synthesis of C-disaccharides of α-d-galactopyranosyl-(1 → 3)-d-galactopyranose (α-Gal), potential tools for studying the biology of α-Gal glycans, is described. The synthetic strategy, centers on the reaction of two easily available precursors 1,2-O-isopropylidene-d-glyceraldehyde and an α-C-glactosyl-E-crotylboronate, which affords a mixture of two diastereomeric anti-crotylation products. The stereoselectivity of this reaction was controlled with (R)- and (S)-TRIP catalysts, and the appropriate diastereomer was transformed to C-linked disaccharides of α-Gal, in which the aglycone segment comprised O-, C- and S-glycoside entities that can enable glycoconjugate synthesis.
View Article and Find Full Text PDFStereoselective synthesis of the northern hemisphere of the proposed structure of neaumycin B.
Org Biomol Chem
September 2024
School of Chemical Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata-700032, India.
The stereoselective synthesis of the northern hemisphere (C-C) of the purported structure of the extremely potent anticancer natural product neaumycin B has been accomplished. Twelve out of nineteen asymmetry centers have been installed chemically. The key highlights of this synthesis include the Krische iridium catalyzed -diastereoselective carbonyl crotylation, the Crimmins aldol reaction, HWE olefination, CBS reduction, vanadium promoted stereoselective epoxidation, Evans methylation and spiroketalization.
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!