Oxazine ring construction: methods and applications to natural product synthesis

Abstract

Although natural products containing a 1,2-oxazine ring are rare, more examples in this family of natural products have been discovered since trichodermamides A and B were reported in 2003. In addition to their structural novelty, these natural products possess very interesting bioactivities that are strongly dependent on their structures, making them attractive targets for investigating structure-activity relationships (SAR). In this feature article, we summarized the methodologies developed in recent years for constructing the 1,2-oxazine rings. Racemic and enantioselective total syntheses of trichodermamides A and B, based on these methodologies, are reviewed in detail.