36379-74-5Relevant academic research and scientific papers
Synthesis of the pyranonaphthoquinones dehydroherbarin, (+)-astropaquinone B and (+)-astropaquinone C en route to ascomycones A and B
Wadsworth, Andrew D.,Sperry, Jonathan,Brimble, Margaret A.
, p. 2604 - 2608 (2010)
The total syntheses of the pyranonaphthoquinone natural products dehydroherbarin, (+)-astropaquinone B and (+)-astropaquinone C are described. A late stage oxidation strategy employed for the synthesis of the astropaquinones was not amenable to the conversion of dehydroherbarin into the ascomycones. The syntheses of astropaquinones B and C reported herein constitute the first total syntheses and their absolute stereochemistry was determined to be (1R,3S). Georg Thieme Verlag Stuttgart New York.
Synthesis of two naphthoquinone antibiotics, dehydroherbarin and 6- deoxybostrycoidin
Kesteleyn, Bart,De Kimpe, Norbert
, p. 640 - 644 (2000)
The synthesis of two naphthoquinone antibiotics, dehydroherbarin (7) and 6-deoxybostrycoidin, was accomplished by reaction of 3-acetonyl-2- bromomethyl-6,8-dimethoxy-1,4-naphthoquinone (23) with either triethylamine or ammonia, respectively. This is the first report on their synthesis.
Heptaketides from Corynespora sp. inhabiting the cavern beard lichen, Usnea cavernosa: First report of metabolites of an endolichenic fungus
Paranagama, Priyani A.,Wijeratne, E. M. Kithsiri,Burns, Anna M.,Marron, Marilyn T.,Gunatilaka, Malkanthi K.,Arnold, A. Elizabeth,Gunatilaka, A. A. Leslie
, p. 1700 - 1705 (2007)
Two new heptaketides, corynesporol (1) and 1-hydroxydehydroherbarin (2), along with herbarin (3) were isolated from an endolichenic fungal strain, Corynespora sp. BA-10763, occurring in the cavern beard lichen Usnea cavernosa. The structures of 1-3 were elucidated from their spectroscopic data. Aerial oxidation of corynesporol (1) yielded herbarin (3). Acetylation of 1 afforded the naphthalene derivative 4, whereas acetylation of 3 gave the corresponding naphthoquinone 6 and dehydroherbarin (5). All compounds were evaluated for their cytotoxicity and ability to inhibit migration of human metastatic breast and prostate cancer cell lines MDA-MB-231 and PC-3M, respectively. Dehydroherbarin (5) inhibited migration of both cell lines at concentrations not toxic to these cell lines. This is the first report of metabolites from an endolichenic fungus.
Applications of [4+2] Anionic Annulation and Carbonyl-Ene Reaction in the Synthesis of Anthraquinones, Tetrahydroanthraquinones, and Pyranonaphthoquinones
Basak, Shyam,Mal, Dipakranjan
, p. 11035 - 11051 (2017/10/27)
Hexa-2,5-dienoates, susceptible to isomerization by acids and bases, are suitable for the [4+2] anionic annulation to give 3-(2-alkenyl)naphthoates in regiospecific manner. When combined with intramolecular carbonyl-ene reaction (ICE), the accessibility of the naphthoates culminates in a new synthesis of anthraquinones and diastereoselective synthesis of tetrahydroanthraquinones. This strategy has also resulted in a 3-step synthesis of dehydroherbarin from a 3-methallylnaphthoate.
The synthesis of the pyranonaphthoquinones dehydroherbarin and anhydrofusarubin using Wacker oxidation methodology as a key step and other unexpected oxidation reactions with ceric ammonium nitrate and salcomine
Pillay, Adushan,Rousseau, Amanda L.,Fernandes, Manuel A.,De Koning, Charles B.
, p. 7809 - 7819 (2013/04/23)
The synthesis of two closely related pyranonaphthoquinones, dehydroherbarin and anhydrofusarubin, is described. The construction of the naphthalene nuclei was achieved using the Stobbe condensation reaction using 2,4- dimethoxybenzaldehyde and 2,4,5-trime
