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., & Moody, C. (2012). Biomimetic Synthesis of the Apoptosis-Inducing Thiazinoquinone Thiaplidiaquinone A. JOURNAL OF ORGANIC CHEMISTRY, 77, 9179-9189 [dx.doi.org/10.1021/jo301738u |].
Data di pubblicazione: | 2012 | |
Titolo: | Biomimetic Synthesis of the Apoptosis-Inducing Thiazinoquinone Thiaplidiaquinone A | |
Autori: | ||
Citazione: | Carbone, A., Lucas, C., & Moody, C. (2012). Biomimetic Synthesis of the Apoptosis-Inducing Thiazinoquinone Thiaplidiaquinone A. JOURNAL OF ORGANIC CHEMISTRY, 77, 9179-9189 [dx.doi.org/10.1021/jo301738u |]. | |
Rivista: | ||
Digital Object Identifier (DOI): | http://dx.doi.org/dx.doi.org/10.1021/jo301738u | | |
Settore Scientifico Disciplinare: | Settore CHIM/08 - Chimica Farmaceutica | |
Appare nelle tipologie: | 1.01 Articolo in rivista |
File in questo prodotto:
File | Descrizione | Tipologia | Licenza | |
---|---|---|---|---|
JOC Natural compound.pdf | N/A | Administrator Richiedi una copia |