109765-65-3Relevant academic research and scientific papers
Synthesis of novel pyranoquinones using an acyl radical cyclization strategy
Donner, Christopher D.,Casana, Myriam I.
scheme or table, p. 1105 - 1107 (2012/04/10)
The thiol-catalysed cyclization of acyl radicals generated directly from benzaldehyde precursors has been investigated. Hindered β- benzyloxyacrylates cyclize efficiently providing a tin-free radical cyclization approach to the serine/threonine kinase AKT inhibitor frenolicin B, whilst γ-aryloxy crotonates give good yields of benzopyran-4-ones. This method is applied to the synthesis of a novel tetracyclic analogue of the pyranonaphthoquinone antibiotics.
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 Natural Compounds with Alkyl-methoxy-1,4-benzoquinone Structure
Pfeifer, Jochen,Gerlach, Hans
, p. 131 - 138 (2007/10/02)
The 1,4-benzoquinones 1-7 occurring in various plants and having interesting biological properties have been synthesized from the tetrahydropyranyl ethers 17 and 21.Reaction with n-butyllithium gave selectively the ortho-lithiated compounds.These could be alkylated with the haloalkenes 13-16 and haloalkanes to give the substituted phenols 18-20 and 22-25 in high yield after methanolysis.Alkylations of the methoxyisopropylether 8 of 10-undecyn-1-ol with bromobutane and bromohexane gave 9 and 10.These alkynols could be selectively hydrogenated with Lindlar-Palladium catalyst to give the (Z)-alkenols 11 and 12 which could be converted into the bromoalkenes 13, 14 and the iodoalkenes 15, 16.Oxidation of the phenols 18-20 and 22-25 with molecular oxygen in the presence of salcomine as catalyst produced the substituted 1,4-benzoquinones 1-3 and 26-29 in high yield.Selective hydrolysis with perchloric acid converted 26-29 into the natural products 4-7. - Key Words: Tetrahydropyranyl-ethers / ortho-Lithiation / ortho-Alkylation / 1,4-Benzoquinones, alkyl-methoxy- / 1,4-Benzoquinones, alkyl-hydroxy-methoxy-
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
Synthesis of Halodimethoxy-1,2-benzoquinones
Wriede, Ulrich,Fernandez, Mario,West, Kevin F.,Harcourt, Dale,Moore, Harold W.
, p. 4485 - 4489 (2007/10/02)
Syntheses of a large number of halodimethoxy-1,2-benzoquinones are described.A key reaction in these syntheses is the chlorination of methoxy-1,2-benzoquinones upon treatment with tert-butyl hypochlorite.
