Streptomyces nitrosporeus

Kim W-G, Kim J-P, Kim C-J, Lee K-H, Yoo I-D (1996) Benzastatins A, B, C, and D New Free Radical Scavengers from Streptomyces nitrosporeus 30643 I. Taxonomy, Fermentation, Isolation, Physico-Chemical Properties and Biological Activities. J Antibiot 49 20... 

C,9H2 C1N03, Mr 351.87, cryst., mp. 59 °C, [ajp -11.1° (CHCI3), an antiviral antibiotic isolated from Streptomyces nitrosporeus. V. inhibits the growth of RNA and DNA viruses (e.g.. Herpes simplex 1 and 2) and has weak antifungal activity. The stereochemistry was revised on the basis of NOE experiments. ... 

In 2009, Nakamura and co-workers [8] developed an organocatalytic aldol reaction between acetaldehyde 4 and dibromoisatin 1 catalyzed by iV-heteroaryl-sulfonylprolinamide 5, to achieve (/ )-convolutamydine E (6) in high enantioselectivity, which was easily converted to (/ )-convolutamydine B (7) (Scheme 17.2). In the same year, the Hayashi group used the prolinol catalyst 10 for the synthesis of enantiomer of natural convolutamydine E ent-6) (Scheme 17.3) [9], and intermediate 12 could be easily transformed into CPC-1 (13), a new pyrrolidinoindoline alkaloid isolated by Takayama and co-workers [10]. In addition, 12 was easily converted to indoline fragment 14, a key intermediate for the syntheses of madindo-line A (15) and B (16), which are selective inhibitors of interleukin-6, isolated from the fermentation broth of Streptomyces nitrosporeus K93-0711 by Omura and coworkers [11]. 

The synthetic practicality of the Meyer-Schuster rearrangement was demonstrated in the synthesis of ( )-virantmycin, a metabolite of Streptomyces nitrosporeus, which has been shown to possess antiviral activity. When the attempted conversion of 17 to 19 via a hydrogenation/cyclization sequence was unsuccessful, an alternate pathway utilizing the Meyer-Schuster reaction was explored. Treatment of 17 with acid was presumed to give the a,P-unsaturated ketone which underwent a spontaneous Michael reaction to give 18. Reduction of the resulting ketone 18 was followed by dehydration to provide 19. 

S. aurantiaca, and Streptomyces nitrosporeus could be potential sources of lead compounds for the rational design of novel agents to treat protozoal diseases. 

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