title: Biomimetic synthesis of the apoptosis-inducing thiazinoquinone thiaplidiaquinone A.
abstract: A concise total synthesis of the apoptosis-inducing, marine metabolite thiaplidiaquinone A is described. The key ring forming steps are both based on biosynthetic considerations and involve the construction of the central benzo[c]chromene quinone unit by an extremely facile oxa-6π-electrocyclic ring closure reaction of an ortho-quinone intermediate, derived by tautomerization of a bis-benzoquinone, readily accessed from two simple phenolic precursors. This is followed by the installation of the 1,4-thiazine-dioxide ring by reaction of the benzo[c]chromene quinone with hypotaurine.
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.
authors.forename: Anna
authors.initials: A
authors.lastname: Carbone
authors.forename: Catherine L
authors.initials: CL
authors.lastname: Lucas
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Moody
mesh_terms: D017209:Apoptosis; D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D011809:Quinones / Q000737:chemistry*; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D011809:Quinones; D013729:Terpenes; C500855:thiaplidiaquinone A