Structure elucidation of nigricanoside A through enantioselective total synthesis

Structure elucidation of nigricanoside A through enantioselective total synthesis

Nigricanoside A was isolated from green alga, and its dimethyl ester was found to display potent cytotoxicity. Its scarcity prevented a full structure elucidation, leaving total synthesis as the only means to determine its relative and absolute stereochemistry and to explore its biological activity. Here we assign the stereochemistry of the natural product through enantioselective total synthes...

Structure elucidation of hypocreolide A by enantioselective total synthesis.

The nonenolide hypocreolide A was isolated from culture filtrates of the ascomycete Hypocrea lactea. It exhibits moderate antimicrobial activity against various tested fungi and bacteria. Since neither the relative nor the absolute stereochemistry of the compound could be initially assigned, a stereochemically flexible total synthesis was developed. The two stereogenic centers were formed in hi...

Structure elucidation of nigricanoside A through enantioselective total synthesis† †Electronic supplementary information (ESI) available: Complete experimental details and characterization data. See DOI: 10.1039/c5sc00281h Click here for additional data file.

Nigricanoside A was isolated from green alga, and its dimethyl ester was found to display potent cytotoxicity. Its scarcity prevented a full structure elucidation, leaving total synthesis as the only means to determine its relative and absolute stereochemistry and to explore its biological activity. Here we assign the stereochemistry of the natural product through enantioselective total synthes...

Enantioselective total synthesis of hyperforin.

A modular, 18-step total synthesis of hyperforin is described. The natural product was quickly accessed using latent symmetry elements, whereby a group-selective, Lewis acid-catalyzed epoxide-opening cascade cyclization was used to furnish the bicyclo[3.3.1]nonane core and set two key quaternary stereocenters.

Enantioselective total synthesis of (-)-jiadifenolide.