Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo961325u | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Cu(II)-NHC Catalyzed Insertion of Quinoid Carbenes into -Epoxides: Stereoselective Synthesis of -Dihydronaphthodioxine.
Org Lett
January 2025
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
A straightforward synthesis of -dihydronaphthodioxine has been efficiently accomplished through Cu(II)-NHC catalysis, involving the stereoselective ring opening of -epoxides with quinoid-carbene. Intramolecular S2-like substitution facilitates the inversion of stereochemistry during -epoxide ring opening. This reaction has been developed under simple conditions, demonstrating a broad substrate scope with a wide chemoselective profile.
View Article and Find Full Text PDFFlow chemistry-enabled asymmetric synthesis of cyproterone acetate in a chemo-biocatalytic approach.
Nat Commun
January 2025
Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai, 200433, China.
Flow chemistry has many advantages over batch synthesis of organic small-molecules in terms of environmental compatibility, safety and synthetic efficiency when scale-up is considered. Herein, we report the 10-step chemo-biocatalytic continuous flow asymmetric synthesis of cyproterone acetate (4) in which 10 transformations are combined into a telescoped flow linear sequence from commercially available 4-androstene-3, 17-dione (11). This integrated one-flow synthesis features an engineered 3-ketosteroid-Δ-dehydrogenase (ReM2)-catalyzed Δ-dehydrogenation to form the C1, C2-double bond of A ring, a substrate-controlled Co-catalyzed Mukaiyama hydration of 9 to forge the crucial chiral C17α-OH group of D ring with excellent stereoselectivity, and a rapid flow Corey-Chaykovsky cyclopropanation of 7 to build the cyclopropyl core of A ring.
View Article and Find Full Text PDFStereoselective Sequential Diels-Alder Reactions on a Cyclic Furan Trimer for the Construction of an Asymmetric Scaffold.
Org Lett
January 2025
Institute of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan.
Multiple Diels-Alder reactions are a powerful method to construct large asymmetric scaffolds, but these reactions often produce numerous isomers. We now report a triple Diels-Alder reaction between a cyclic furan trimer and -substituted maleimides, achieving selective synthesis of a single asymmetric tris-adduct. The stereoselectivity of cycloaddition to π-extended furan derivatives was clarified by the experimental analysis of intermediates and theoretical calculations.
View Article and Find Full Text PDFTranscriptome Analysis of and Functional Validation of CYP80s Involved in Benzylisoquinoline Alkaloid Biosynthesis.
Molecules
January 2025
State Key Laboratory for Quality Ensurance and Sustainable Use of Dao-di Herbs, National Resource Center for Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China.
The medicinal plant is rich in aporphine alkaloids, a type of benzylisoquinoline alkaloid (BIA), with aporphine being the representative and most abundant compound, but our understanding of the biosynthesis of BIAs in this plant has been relatively limited. Previous research reported the genome of and preliminarily identified the norcoclaurine synthase (NCS), which is involved in the early stages of the BIA biosynthetic pathways. However, the key genes promoting the formation of the aporphine skeleton have not yet been reported.
View Article and Find Full Text PDFConstruction of Axially Chiral Tetra-ortho-Substituted Biaryls by Palladium-Catalyzed Asymmetric Suzuki-Miyaura Coupling.
Chem Asian J
January 2025
Nanjing University, School of Chemistry and Chemial Engineering, 163 Xianlin Avenue, 210023, Nanjing, CHINA.
Axial chiral biaryl skeletons are widely found in biologically active molecules, catalysts and chiral functional materials. However, highly catalytic stereoselective synthesis of tetra-ortho-substituted biaryls remains a challenging task. In this paper, we describe an efficient approach for construction of axially tetra-ortho-substituted biaryls via Suzuki-Miyaura coupling in the presence of a chiral monophosphate ligand developed by ourselves.
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!