A stereoselective decarboxylative aldol addition of β- and α-keto acids in the presence of catalytic amounts of amines is described. By the optional deployment of chiral enolizable aldehydes an access to enantiopure configurative defined ketopentoses, ketohexoses, or ketoheptoses is given.
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http://dx.doi.org/10.1021/ol200412r | DOI Listing |
J Am Chem Soc
November 2024
School of Pharmacy, Fudan University, Shanghai, China, 201203.
Norzoanthamine is a structurally complex polycyclic natural product that expresses a broad range of biological activities, rendering facile access to it and its analogs of considerable importance in drug discovery and development. However, strategies for efficient access to this class of marine alkaloids remain lacking. Here, we report a strategy, characterized by three key photochemical reactions, that we used to synthesize norzoanthamine in 16 steps.
View Article and Find Full Text PDFChembiochem
October 2024
State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
Modular type I polyketide synthases (PKSs) are remarkable molecular machines that can synthesize structurally complex polyketide natural products with a wide range of biological activities. In these molecular machines, ketosynthase (KS) domains play a central role, typically by catalyzing decarboxylative Claisen condensation for polyketide chain extension. Noncanonical KS domains with catalytic functions rather than Claisen condensation have increasingly been evidenced, further demonstrating the capability of type I PKSs for structural diversity.
View Article and Find Full Text PDFOrg Lett
October 2024
Chemistry Program, New York University Abu Dhabi (NYUAD), Saadiyat Island, United Arab Emirates.
Herein, we report the application of a benzyloxy-functionalized malonic acid half thioester as an activated ester equivalent in a highly enantioselective decarboxylative glycolate aldol reaction. This robust method operates at ambient temperature, tolerates air and moisture, and generates CO as the only byproduct. The synthetic applicability of the method is demonstrated by the large-scale enantiodivergent synthesis of α-benzyloxy-β-hydroxybutyric acid thioester and its subsequent conversion to diverse polyoxygenated building blocks, deoxy-sugars, and (-)-angiopterlactone B.
View Article and Find Full Text PDFSheng Wu Gong Cheng Xue Bao
September 2024
Key Laboratory of Bioorganic Synthesis of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, Zhejiang, China.
Polymers (Basel)
July 2024
Departamento de Ingeniería de Maderas, Universidad del Bío-Bío, Concepción 4081112, Chile.
Catalytic biomass pyrolysis is one of the most promising routes for obtaining bio-sustainable products that replace petroleum derivatives. This study evaluates the production of aromatic compounds (benzene, toluene, and xylene (BTX)) from the catalytic pyrolysis of lignocellulosic biomass ( (PR) and (EG)). Chilean natural zeolite (NZ) was used as a catalyst for pyrolysis reactions, which was modified by double ion exchange (H2NZ) and transition metals impregnation (Cu5H2NZ and Ni5H2NZ).
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