Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 20, Pages 9179-9189Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301738u
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Funding
- EU for a Marie Curie Fellowship
- Engineering and Physical Sciences Research Council via the DTA scheme
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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-6 pi-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.
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