79971-33-8Relevant academic research and scientific papers
Synthesis of naturally occurring pyranonaphthoquinones: (±) 9-demethoxyeleutherin, (±) 9-demethoxyisoeleutherin, and pentalongin via nef reaction
Limaye, Rohan A.,Natu, Arun D.,Paradkar, Madhusudan V.
, p. 2503 - 2509 (2014/08/05)
GRAPHICAL ABSTRACT The article describes alternative method for the synthesis of (±) 9-demethoxyeleutherin and (±) 9-demethoxyisoeleutherin, the analogs of naturally occurring pyranonaphthoquinones antibiotics eleutherin and isoeleutherin. This methodology has provided the target molecules using a shorter route involving five simple chemical transformations with Nef reaction as a key step. All the intermediates and target molecules were completely characterized by spectral techniques and confirmed by comparison with literature data. Further we have extended Nef protocol toward formal synthesis of naturally occuring pyranonaphthoquinone pentalongin. We accomplished synthesis of of 2-(1,4-dimethoxynaphthalen-2-yl) acetic acid devoid of very toxic cyanide intermediates, which has been converted into pentalongin.
Simple synthesis of two naphthoquinone antibiotics psychorubrin and pentalongin
Bulbule, Vivek J.,Koranne, Priti S.,Munot, Yogesh S.,Borate, Hanumant B.,Deshpande, Vishnu H.
, p. 587 - 594 (2007/10/03)
1H-Naphtho[2,3-c]pyran-5,10-dione derivatives were synthesized using chloromethylation of substituted-2-naphthylacetic acid as the key step. The utility of this method was demonstrated in the synthesis of two-pyranonaphthoquinone antibiotics psychorubrin (1) and pentalongin (2).
The synthesis of radermachol
Joshi,Jiang,Rho,Pelletier
, p. 8220 - 8232 (2007/10/02)
Five different approaches to the preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (3), an intermediate needed for the synthesis of radermachol (1), the red pigment from the roots of Radermachera xylocarpa, are described. The synthesis of radermachol (1) has been accomplished from 1,4-naphthoquinone in 14 steps.
