title: Convergent synthesis and structural confirmation of phellodonin and sarcodonin ε.
abstract: The first synthesis of members of the sarcodonin family, phellodonin and sarcodonin ε, is reported herein. This verifies that the unprecedented and seemingly unstable N,N-dioxide-containing benzodioxazine framework can be constructed in the laboratory and lends further support to the proposed structures. The key step in the synthesis involves a biomimetic hetero-Diels-Alder reaction between a pyrazine N-oxide and an ortho-quinone.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Ippei
authors.initials: I
authors.lastname: Usui
authors.forename: David W
authors.initials: DW
authors.lastname: Lin
authors.forename: Takeshi
authors.initials: T
authors.lastname: Masuda
authors.forename: Phil S
authors.initials: PS
authors.lastname: Baran
mesh_terms: D003497:Cyclic N-Oxides / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D011719:Pyrazines / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003497:Cyclic N-Oxides; D011719:Pyrazines; D011809:Quinones; D013729:Terpenes; C583643:phellodonin; C117589:sarcodonin M