title: Establishment of benzodioxazine core structure for sarcodonin class of natural products by X-ray analysis.
abstract: Sarcodonin ε (2), isolated from Sarcodon scabrosus, was treated with trimethylsilyldiazomethane to yield a crystalline methylated derivative 6. The structure of 6 was determined by X-ray analysis, which confirmed the presence of an unprecedented N(1b)-OMe group, the configuration at N(1b) and the 1,3,4-substituted phenyl ring structure of 2. More importantly, the structures of 6 and 2 have answered the intriguing problem of solving the core structure of the sarcodonin class of natural products, establishing that sarcodonins have a benzodioxazine core structure, rather than the recently proposed benzodioxane aminal core structure.
authors.affiliation: Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Tokyo 152-8551, Japan.
authors.forename: Hironori
authors.initials: H
authors.lastname: Masubuti
authors.forename: Yasuhisa
authors.initials: Y
authors.lastname: Endo
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Araya
authors.forename: Hidehiro
authors.initials: H
authors.lastname: Uekusa
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Fujimoto
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry
chemical_list: D001688:Biological Products; D010078:Oxazines; D013729:Terpenes; C117589:sarcodonin M