A concise total synthesis of the apoptosisinducing, 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
Carbone, A., Lucas, C.L., Moody, C.J. (2012). Biomimetic Synthesis of the Apoptosis-Inducing Thiazinoquinone Thiaplidiaquinone A. JOURNAL OF ORGANIC CHEMISTRY, 77, 9179-9189 [dx.doi.org/10.1021/jo301738u |].
Biomimetic Synthesis of the Apoptosis-Inducing Thiazinoquinone Thiaplidiaquinone A
CARBONE, Anna;
2012-01-01
Abstract
A concise total synthesis of the apoptosisinducing, 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 hypotaurineFile | Dimensione | Formato | |
---|---|---|---|
JOC Natural compound.pdf
Solo gestori archvio
Dimensione
502.34 kB
Formato
Adobe PDF
|
502.34 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.