Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry.

Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry† †Electronic supplementary information (ESI) available: Experimental details and spectral data are provided. CCDC 1489617. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc03578g Click here for additional data file. Click here for additional data file.

[Development of new synthetic methods and their application to synthesis of useful compounds].

Development of novel synthetic methodologies and their application to synthesis of natural products are described. The first topic is about an extension of the scope of our indole synthesis by radical cyclization of o-alkenylphenyl isocyanides. By utilizing this methodology and nitrogenzenesulfonamide chemistry, an efficient total synthesis of hexacyclic aspidosperma indole alkaloid, aspidophyt...

Total synthesis and absolute configuration of nocardioazine B.

The first total synthesis of the indole alkaloid nocardioazine B was accomplished in 10 steps with an overall yield of 11.8%, establishing the absolute stereochemistry of the natural product.

Stereospecific Total Synthesis of the Indole Alkaloid Ervincidine. Establishment of the C-6 Hydroxyl Stereochemistry

The total synthesis of the indole alkaloid ervincidine (3) is reported. This research provides a general entry into C-6 hydroxy-substituted indole alkaloids with either an α or a β configuration. This study corrects the errors in Glasby's book (Glasby, J. S. Encyclopedia of the Alkaloids; Plenum Press: New York, 1975) and Lounasmaa et al.'s review (Lounasmaa, M.; Hanhinen, P.; Westersund, M. In...

Isolation and complete structural assignment of Lycopodium alkaloid cernupalhine A: theoretical prediction and total synthesis validation.

Cernupalhine A (1) is a trace Lycopodium alkaloid (0.7 mg) possessing a new C17N skeleton with an unusual hydroxydihydrofuranone motif newly isolated from Palhinhaea cernua L. Its complete structural assignment, including absolute stereochemistry, was established through a combination of high-field NMR techniques and computational methods and further unequivocal confirmation by the first asymme...