Isolation and Biological Activity

The number of total syntheses of lentiginosine and 2-ept-lentiginosine pub-Ushed since the previous synopsis in these volumes is truly staggering almost 

1 Routes Employing Late-Stage C-1/C-2 Bond Formation 

2 Routes Employing Late-Stage Alkylative C-3/N Bond Formation 

The concise route to (+)-lentiginosine (127) and its (lS,2S,7J .,8aS)-(+)-7 hydroxy analog by Goti et al., originally reported in a communication and previously described in this series, has since been pubHshed with full experimental details. 

---

Pacey, M.S., Dirlam, J.P., Geldart, R.W. et al. (1998) Novel erythromycins from a recombinant Saccharopolyspora erythraea strain NRRL 2338 pIGl. I. Fermentation, isolation and biological activity. The Journal of Antibiotics, 51, 1029. 

Koguchi, Y., Kohno, J., Nishio, M., Takahashi, K., Okuda, T., Ohnuki, T., and Komatsubaea, S. TMC-95A, B, C, and D, novel proteasome inhibitors produced by Apiospora montagnei Sacc. TC 1093. Taxonomy, production, isolation, and biological activities. J Antibiot (Tokyo) 2000, 53, 105-109. 

Mori H, Urano Y, Abe F, Furukawa S, Tsurumi Y, Sakamoto K, Hashimoto M, Takase S, Fiino M, Fujii T. (2003) FR235222, a fungal metabolite, is a novel immunosuppressant that inhibits ammalian histone deacetylase (HDAC). 1. Taxonomy, fermentation, isolation and biological activities. J Antibiot 56 72-79. 

Kuno F, Otoguro K, Shiomi K, et ai, Arisugacins A and B, novel and selective acetylcholinesterase inhibitors from Penicillium sp FO-4259.1. Screening, taxonomy, fermentation, isolation and biological activity, f Antibiot, 49 742-746, 1996. 

Stadler M etal., Lachnumon and lachnumol A, new metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst.) Karst. I. Producing organism, fermentation, isolation and biological activities,... 

Takahashi, S., Watanabe, K., Saito, S. and Nomura, Y. (1995). Isolation and biological activity of the sex pheromone of the smoky brown cockroach, Periplaneta fuliginosa Serville (Dictyoptera Blattidae). Applied Entomology and Zoology 30 357-360. 

Lee CH, Chung MC, Lee HJ, Bae KS, Kho YH (1997) MR566A and MR566B, New Melanin Synthesis Inhibitors Produced by Trichoderma harzianum I. Taxonomy, Fermentation, Isolation and Biological Activities. J Antibiot 50 469... 

Stadler M, Anke H, Sterner O (1995) Metabolites with Nematicidal and Antimicrobial Activities from the Ascomycete Lachnum papyraceum (Karst.) Karst V. Production, Isolation and Biological Activities of Bromine-Containing Mycorrhizin and Lachnumon Derivatives and Four Additional New Bioactive Metabolites. J Antibiot 48 149... 

Matsuzaki K, Ikeda H, Masuma R, Tanaka H, Omura S (1995) Isochromophilones I and II, Novel Inhibitors against gpl20-CD4 Binding Produced by Penicillium multicolor FO-2338 I. Screening, Taxonomy, Ferrmentation, Isolation and Biological Activity. J Antibiot 48 703... 

Engler M, Anke T, Sterner O, Brandt U (1997) Pterulinic Acid and Pterulone, Two Novel Inhibitors of NADH Ubiquinone Oxidoreductase (Complex I) Produced by a Pterula Species I. Production, Isolation and Biological Activities. J Antibiot 50 325... 

S Omura, D Van der Pyl, J Inokoshi, Y Takahashi, H Takeshima. Pepticinnamins, new farnesyl-protein transferase inhibitors produced by an actinomycete. I. Producing strain, fermentation, isolation and biological activity. J Antibiot 46 222-228, 1993. 

Weibel EK, Hadvary P, Hochuli E, Kupfer E, Lengsfeld H (1987) Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity. J Antibiot 40 1081-1085... 

Mutoh M, NakadaN, Matsukuma S, Ohshima S, Yoshinari K, Watanabe J, Arisawa M (1994) Panclicins, novel pancreatic lipase inhibitors I. Taxonomy, fermentation, isolation and biological activity. J Antibiot 47 1369-1375... 

Morita, T., Ohtsubo, S., Nakamura, T., Tanaka, S., Iwanaga, S., Ohashi, K., Niwa, M. Isolation and biological activities of limulus anticoagulant (anti-LPS factor) which interacts with lipopolysaccharide (LPS). J Biochem (Tokyo) 97 (1985b) 1611-1620. 

Nakano, H., Matsuda, Y., Ito, K., Ohkubo, S., Morimoto, M., and Tomita, F. 1981. Gilvocarcins, new antitumor antibiotics. 1. Taxonomy, fermentation, isolation and biological activities. J. Antibiot. (Tokyo) 34, 266-270. 

Burkhardt, K. Fiedler, H.P. Grabley S. Thierick, e.R. Zeeck, A. New Cineromycins and Musacins Obtained by Metabolite Pattern Analysis of Sterp-tomyces griseoviridis (FH-S 1832)—1. Taxonomy, Fermentation, Isolation and Biological Activity, J. Antibiot. 49(5), 432-437 (1996). 

Sanglier, J. J., Quesniaux, V., Fehr, T., Hofmann, H., Mahnke, M., Memmert, K., Schuler, W., Zenke, G., Gschwind, L., Maurer, C., and Schilling, W. (1999). Sanglifehrins A, B, C and D, novel cyclophilin-binding compounds isolated from Streptomyces sp. A92-308110. I. Taxonomy, fermentation, isolation and biological activity. J. Antibiot. 52,466-473. 

Femandez-Chimeno, I. R., Canedo, L., Espliego, R, Gravalos, D., De La Calle, F, Femandez-Puentes, J. L., and Romeo, F. (2000). IB-96212, a novel cytotoxic macrolide produced by a marine Micromonospora. I. Taxonomy, fermentation, isolation and biological activities. J. Antibiot. 53,474-478. 

Abstract- The isolation and biological activity of several sesquiterpenes classified as phytoalexin are described. The synthesis of these sesquiterpenes, are described. Several routes have been developed to synthesize a particular sesquiterpenes. 

---