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 hypotaurine
Settore CHIM/08 - Chimica Farmaceutica
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 |].
File in questo prodotto:
File 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.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/66388
Citazioni
  • ???jsp.display-item.citation.pmc??? 6
  • Scopus 21
  • ???jsp.display-item.citation.isi??? 21
social impact