6533b83afe1ef96bd12a7993
RESEARCH PRODUCT
Biomimetic Synthesis of the Apoptosis-Inducing Thiazinoquinone Thiaplidiaquinone A
Anna CarboneCatherine L. LucasChristopher J. Moodysubject
Molecular StructureTerpenesStereochemistryMetaboliteOrganic ChemistryQuinonesTotal synthesisApoptosisHypotaurineThiaplidiaquinone A natural compoundsRing (chemistry)TautomerSettore CHIM/08 - Chimica FarmaceuticaQuinonechemistry.chemical_compoundchemistryBiomimetic MaterialsApoptosisBiomimetic synthesisThiaplidiaquinone A; natural compoundsnatural compoundsThiaplidiaquinone Adescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2012-01-01 |