76959-18-7Relevant academic research and scientific papers
Synthesis of antibiotics WS 5995 A and C and related compounds by palladium-catalyzed coupling of 2-bromonaphthoquinones with organostannanes
Echavarren,Tamayo,Cardenas
, p. 6075 - 6083 (2007/10/02)
The synthesis of arylnaphthoquinones can be performed simply by using as the key reaction the Pd(0)- and Cu(I)-catalyzed coupling of arylstannanes with 2-bromonaphthoquinones as the electrophiles. The palladium-catalyzed coupling reaction is general and allows for the functionalization of the unprotected quinone nucleus with alkyl, alkenyl, and aryl substituents. The coupling process tolerates the presence of a chelated peri hydroxyl and steric crowding of a 2,6-disubstituted arylstannane, although the preparation of a 2,6,2',6'-tetrasubstituted biaryl by coupling of 2-bromo-3,5-bis(acetyloxy)-1,4-naphthoquinone as the electrophile with 2,6-disubstituted arylstannanes was unsuccessful. The syntheses of quinonoid antibiotics WS 5995 A and C was accomplished by using this method as the key step. Benz[b]phenanthridinone 1, hypothetical intermediate in the biosynthesis of benz[b]phenanthridine alkaloids, was also prepared from antibiotic WS 5995 C or by addition of ammonia to the 2-aryl-1,4-naphthoquinone 41 followed by heterocyclization.
1,4-Naphtoquinone derivatives and their use in treating coccidiosis
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, (2008/06/13)
1,4-naphthoquinone derivatives represented by the following general formula: STR1 (wherein R1 represents a hydrogen atom, a hydroxy group, a lower alkoxy group or an arylthio group, R2 represents a carboxy group, an esterified carbox
STRUCTURE ELUCIDATION AND SYNTHESIS OF A NEW ANTICOCCIDICAL SUBSTANCE ISOLATED FROM STREPTOMYCES AURANTICOLOR
Tanaka, Hirokazu,Itoh, Yoshikuni,Ikushima, Hiroichi,Okamoto, Masanori,Kawai, Yoshio,Imanaka, Hiroshi
, p. 4359 - 4360 (2007/10/02)
The structure elucidation and synthesis of WS 5995, produced by Streptomyces auranticolor, were described.
