Despite the unique and impressive complexity of the chartellines and related natural products isolated over 15 years ago from marine bryozoans, there have been no studies directed towards the synthesis of these compounds. Plausible synthetic pathways leading to this unexplored class of unprecedented alkaloids, facilitated by new synthetic methodologies and designed cascade reactions, have been put forth based upon a postulated unifying biogenetic hypothesis. Due to the sensitive nature of these natural products coupled with their difficulty in reisolation, synthetic routes to these compounds will provide significant quantities of the natural products themselves as well as analogs otherwise unavailable to potentially serve as biological tools. A number of new synthetic methods and tactics for the construction of polycyclic indole and imidazole-based alkaloids will also be developed. Thus, the significance of this work resides in its promise to advance enabling technologies for drug discovery and development in the areas of synthetic organic chemistry and chemical biology.
| Fujiwara, Yuta; Dixon, Janice A; Rodriguez, Rodrigo A et al. (2012) A new reagent for direct difluoromethylation. J Am Chem Soc 134:1494-7 |
| Michaudel, Quentin; Thevenet, Damien; Baran, Phil S (2012) Intermolecular Ritter-type C-H amination of unactivated sp3 carbons. J Am Chem Soc 134:2547-50 |
