109765-65-3Relevant articles and documents
Biomimetic synthesis of the apoptosis-inducing thiazinoquinone thiaplidiaquinone A
Carbone, Anna,Lucas, Catherine L.,Moody, Christopher J.
, p. 9179 - 9189 (2013/01/15)
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-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.
Synthesis of 2,2-dimethyl-3, 4-epoxy-2h-naphtho[2,3-b]pyran-5, 10-dione
Tapia,Lizama,Lopez,Valderrama
, p. 601 - 606 (2007/10/03)
A short and convenient synthesis of benzopyranoquinone 6 and its application to the preparation of epoxynaphthopyanoquinone 1 is described.
Synthesis of (S)-4-hydroxy-α-lapachone and biotransformation of some 4-chromanones by Mortierella isabellina ATCC 42613
Holland,Qi,Manoharan
, p. 1399 - 1405 (2007/10/03)
1-Methoxy-2-naphthol was converted by MOM ether formation, lithiation at C-3, reaction with 3,3-dimethylacryloyl chloride, cyclization, and oxidation using cerium ammonium nitrate to 4-keto-α-lapachone (2,2-dimethyl-4-keto-1-oxa-1,2,3,4-tetrahydroanthra-5