Biomimetic Synthesis of the Apoptosis-Inducing ThiazinoquinoneThiaplidiaquinone A

Anna Carbone, Christopher J. Moody, Catherine L. Lucas, Anna Carbone

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20 Citations (Scopus)


A concise total synthesis of the apoptosisinducing,marine metabolite thiaplidiaquinone A is described.The key ring forming steps are both based on biosyntheticconsiderations and involve the construction of the centralbenzo[c]chromene quinone unit by an extremely facile oxa-6π-electrocyclic ring closure reaction of an ortho-quinoneintermediate, 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-dioxidering by reaction of the benzo[c]chromene quinone with hypotaurine
Original languageEnglish
Pages (from-to)9179-9189
Number of pages11
JournalJournal of Organic Chemistry
Publication statusPublished - 2012

All Science Journal Classification (ASJC) codes

  • Organic Chemistry


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