Natural product synthesis articles from across Nature Portfolio

Zwitterionic polysaccharides present on the surface of a common gut commensal Bacteroides fragilis are considered to be potential antigens for the development of totally carbohydrate-based vaccines. Here, the authors report the total synthesis of a highly branched phosphorylated zwitterionic capsular hexasaccharide repeating unit of Bacteroides fragilis via a one-pot glycosylation strategy.

The Veratrum alkaloids are a class of highly intricate natural products renowned for their complex structural and stereochemical characteristics. Herein, the authors report the divergent synthesis of zygadenine, germine, protoverine and the alkamine of veramadine A, capitalizing on a late-stage neighboring group participation.

Stereoselective synthesis of tetrahydro-βcarboline skeletons have immense impacts and attract enormous attention. Here, the authors report chiral phosphoric acid catalyzed asymmetric 1,3-dipolar cycloaddition, affording three types of chiral tetrahydro-β-carbolines bearing continuous multi-chiral centers and quaternary chiral centers.

The complex and diverse molecular architectures along with broad biological activities of ent-kauranoids natural products attract increasing interest from synthetic chemists. Herein, the authors report the enantioselective total syntheses of C-19 oxygenated enmein-type ent-kauranoids, including (–)-macrocalyxoformins A and B and (–)-ludongnin C.

Eunicellane diterpenoids are bioactive compounds with a typical 6,10-bicycle, and their scaffolds exhibit innate structural flexibility, but the mechanistic basis for controlling flexibility was unknown. Here, the authors report a genome mining-based discovery of a terpene synthase, MicA, that synthesizes a nearly non-flexible eunicellane skeleton, and propose that configurations of bridging carbons and their adjacent double bond govern flexibility in eunicellane structures.

Structurally diverse natural products are a promising source of antibiotics. Here, the authors report the collective asymmetric total synthesis of polycyclic xanthene myrtucommulone D and five related congeners and discover a compound active against both drug-sensitive and drug-resistant Staphylococcus aureus.

Enantioselective hydrogenation is a stalwart reaction in synthetic chemistry. Now, hydrogenation of tetrasubstituted 1,2-dihydronaphthalene esters gives access to more than 30 cyclolignan natural products.

Owing to its structural complexity, the total synthesis of alchivemycin A has proved challenging. Now, the total synthesis of alchivemycin A is achieved using a chemoenzymatic approach that combines de novo skeleton construction with a late-stage enzymatic oxidation cascade. Following rational protein engineering of a key enzyme, the final product is obtained in high yield.

Enantioselective electrocatalysis is emerging as an increasingly versatile tool in organic synthesis. Now, by applying asymmetric Lewis acid catalysis with an elaborated ligand design, radical electrochemical amination is accomplished with full selectivity control.

The synthesis of natural products with important biological properties has always fascinated chemists, but the development of rapid, efficient and stereoselective transformations remains challenging. Now, a strategy has been developed to produce several strychnan alkaloids through formation of a common bridged morphan core structure.