Streptomyces prunicolor

Benthoeyanin A is a powerful radical scavenger from the mycelium of Streptomyces prunicolor. A new route to phenazine is described via the Pd(II)-catalyzed intramolecular amination of aryl bromide [9]. Treatment of 2-bromo-3-nitro-methylbenzoate (230) and 6-aminobenzofuran derivatives 231 with Pd(OAc)2 gave nitrodiphenylamine 232 in 99%. Catalytic hydrogenation of 232 followed by bromination gave the phenylenedi-amine derivative 233 in 91% yield. Cyclization of the diamine 233 provided the key intermediate phenazine 234. 

Benthoeyanin A is a powerful radical scavenger from the mycelium of Streptomyces prunicolor. A new route to phenazine was described via the Pd-catalyzed intramolecular amination of aryl bromide [158]. 

Compound (80), a structural isomer of umuravarumbolide (55), is a minor constituent of Cryptocarya latifolia 89). The immunosuppressive agent, (—)-PA-48153 (81), has been isolated from Streptomyces prunicolor sp. PA 48153 (90). The same compound, obtained from Streptomyces sp. NK10958 and shown to be a plant growth regulator, has been named pironetin, and the structure based on spectral data, confirmed by X-ray analysis 91, 92) and synthesis 93). 

Yoshida, T., K. Koizumi, Y. Kawamura, K. Matsumoto, and H. Itazaki Lactone with Immunosuppresive Activity and its Manufacture with Streptomyces prunicolor. European Patent 560389 (1993). 

Yasui K, Tamura Y, Nakatani T, Horibe I, Kawada K, Koizumi K, Suzuki R, Ohtani M. Chemical modification of PA-48153C, a novel immunosuppressant isolated from Streptomyces prunicolor PA-48153. J. Antibiot. 1996 49 173 80. 

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