Pyrrole and Its Derivatives

Heterocycles in Natural Product Synthesis

Volumn , Issue , 2011, Pages 187-220

  Mal, Dipakranjan ^a   Shome, Brateen ^a   Dinda, Bidyut Kumar ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Common ring heterocycles; Heterocycles; Natural products; Pyrrole; Synthesis

Indexed keywords

EID: 84859806662     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527634880.ch6     Document Type: Chapter

References (105)

1. Joule, J.A. and Mills, K. (2010) Heterocyclic Chemistry, John Wiley & Sons, Ltd, Chichester, UK.
2. Paal, C. (1885) Synthese von Thiophen -und Pyrrolderivaten. Ber. Dtsch. Chem. Ges., 18, 367-371.
3. Knorr, L. (1885) Einwirkung des Diacetbernsteins ä ureesters auf Ammoniak und prim äre Aminbasen. Ber. Dtsch. Chem. Ges., 18, 299-311.
4. Taylor, E.C. and Jones, R.A. (1990) Pyrroles, John Wiley & Sons, Inc., New York, USA
5. Gilchrist, T.L. (1997) Heterocyclic Chemistry, 3rd edn, Addison Wesley Longman, Essex, UK.
6. Walsh, C.T., Garneau-Tsodikova, S. and Howard-Jones, A.R. (2006) Biological formation of pyrroles: nature's logic and enzymatic machinery. Nat. Prod. Rep., 23, 517-531.
7. Rapoport, H. and Holden, K.G. (1962) The synthesis of prodigiosin. J. Am. Chem. Soc., 84 (4), 635-642.
8. O'Hagan, D. (2000) Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids. Nat. Prod. Rep., 17, 435-446
9. Liddell, J.R. (2002) Pyrrolizidine alkaloids. Nat. Prod. Rep., 19, 773-781.
10. Ebada, S.S., Edrada-Ebel, R., de Voogd, N.J., Wray, V. and Proksch, P. (2009) Dibromopyrrole alkaloids from the marine sponge Acanthostylotella sp. Nat. Prod. Commun., 4 (1), 47-52.
11. Zhang, D.S., Gao, H.Y., Song, X.M., Tang, Z.S. and Wu, L.J. (2008) A new alkaloid from Castanea mollissima Blume. Chin. Chem. Lett., 19 (7), 832-834.
12. Kuramoto, M., Miyake, N., Ishimaru, Y., Ono, N. and Uno, H. (2008) Cylindradines A and B: novel bromopyrrole alkaloids from the marine sponge Axinella cylindratus. Org. Lett., 10 (23), 5465-5468.
13. Aiello, A., D'Esposito, M., Fattorusso, E., Menna, M., Müeller, W.E.G., Perovi_UNDEFINED-Ottstadt, S., Tsuruta, H., Gulder, T.A.M. and Bringmann, G. (2005) Daminin, a bioactive pyrrole alkaloid from the mediterranean sponge Axinella damicornis. Tetrahedron, 61 (30), 7266-7270.
14. Zennie, T.M. and Cassady, J.M. (1990) Funebradiol, a new pyrrole lactone alkaloid from Quararibea funebris flowers. J. Nat. Prod., 53 (6), 1611-1614.
15. Dong, Y., Pai, N.N., Ablaza, S.L., Yu, S.X., Bolvig, S., Forsyth, D.A. and Le Quesne, P.W. (1999) Quararibea metabolites. 4.Total synthesis and conformational studies of (±)-funebrine and (±)-funebral. J. Org. Chem., 64 (8), 2657-2666.
16. Macherla, V.R., Liu, J., Bellows, C., Teisan, S., Nicholson, B., Lam, K.S. and Potts, B.C.M. (2005) Glaciapyrroles A, B, and C, pyrrolosesquiterpenes from a Streptomyces sp. isolated from an Alaskan marine sediment. J. Nat. Prod., 68 (5), 780-783.
17. Eder, C., Proksch, P., Wray, V., Steube, K., Bringmann, G., van Soest, R.W.M., Sudarsono, S., Ferdinandus, E., Pattisina, L.A., Wiryowidagdo, S. and Moka, W. (1999) New alkaloids from the Indopacific sponge Stylissa carteri. J. Nat. Prod., 62 (1), 184-187.
18. Mangu, N., Spannenberg, A., Beller, M. and Tse, M.K. (2010) Synthesis of novel annulated hymenialdisine analogues via palladium-catalyzed cross-coupling reactions with arylboronic acids. Synlett, (2), 211-214.
19. Chang, L.C., Otero-Quintero, S., Hooper, J.N.A. and Bewley, C.A. (2002) Batzelline D and isobatzelline E from the Indopacific sponge Zyzzya fuliginosa. J. Nat. Prod., 65 (5), 776-778.
20. Tao, X.L., Cheng, J.F., Nishiyama, S. and Yamamura, S. (1994) Synthetic studies on tetrahydropyrroloquinoline -containing natural products: syntheses of discorhabdin C, batzelline C and isobatzelline C. Tetrahedron, 50 (7), 2017-2028.
21. Krishnaiah, P., Reddy, V.L.N., Venkataramana, G., Ravinder, K., Srinivasulu, M., Raju, T.V., Ravikumar, K., Chandrasekar, D., Ramakrishna, S. and Venkateswarlu, Y. (2004) New lamellarin alkaloids from the Indian ascidian Didemnum obscurum and their antioxidant properties. J. Nat. Prod., 67 (7), 1168-1171.
22. Fan, H., Peng, J., Hamann, M.T. and Hu, J.F. (2008) Lamellarins and related pyrrole-derived alkaloids from marine organisms. Chem. Rev., 108 (1), 264-287.
23. Cafieri, F., Fattorusso, E. and Taglialatela-Scafati, O. (1998) Novel bromopyrrole alkaloids from the sponge Agelas dispar. J. Nat. Prod., 61 (1), 122-125.
24. Sun, X.T. and Chen, A. (2007) Total synthesis of rac-longamide B. Tetrahedron Lett., 48 (19), 3459-3461.
25. Aiello, A., D'Esposito, M., Fattorusso, E., Menna, M., Müller, W.E.G., Perović-Ottstadt, S. and Schroeder, H.C. (2006) Novel bioactive bromopyrrole alkaloids from the mediterranean sponge Axinella verrucosa. Biol. Med. Chem., 14 (1), 17-24.
26. Woo, J.C.S. and MacKay, D.B. (2003) Diastereoselective isothiourea iodocyclization for manzacidin synthesis. Tetrahedron Lett., 44 (14), 2881-2883.
27. Boonlarppradab, C., Kauffman, C.A., Jensen, P.R. and Fenical, W. (2008) Marineosins A and B, cytotoxic piroaminals from a marine-derived actinomycete. Org. Lett., 10 (24), 5505-5508.
28. Hughes, C.C., Prieto-Davo, A., Jensen, P.R. and Fenical, W. (2008) The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp. Org. Lett., 10 (4), 629-631
29. Hughes, C.C., Kauffman, C.A., Jensen, P.R. and Femical, W. (2010) Structures, reactivities, and antibiotic properties of the marinoprroles A-F. J. Org. Chem., 75 (10), 3240-3250.
30. Uemoto, H., Tsuda, M. and Kobayashi, J. (1999) Mukanadins A-C, new bromopyrrole alkaloids from marine sponge Agelas nakamurai. J. Nat. Prod., 62 (11), 1581-1583.
31. Crestia, D., Demuynck, C. and Bolte, J. (2004) Transketolase and fructose-1,6 -bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues. T etrahedron, 60 (10), 2417-2425.
32. Endo, T., Tsuda, M., Okada, T., Mitsuhashi, S., Shima, H., Kikuchi, K., Mikami, Y., Fromont, J. and Kobayashi, J. (2004) Nagelamides A-H, new dimeric bromopyrrole alkaloids from marine sponge Agelas species. J. Nat. Prod., 67 (8), 1262-1267.
33. Liu, R., Liu, Y., Zhou, Y.D. and Nagle, D.G. (2007) Molecular-targeted antitumor agents. 15. neolamellarins from the marine sponge Dendrilla nigra inhibit hypoxia-inducible factor-1 activation and secreted vascular endothelial growth factor production in breast tumor cells. J. Nat. Prod., 70 (11), 1741-1745.
34. Arafeh, K.M. and Ullah, N. (2009) Synthesis of neolamellarin A, an inhibitor of hypoxia-inducible factor-1. Nat. Prod. Commun., 4 (7), 925-926.
35. Hopp, D.C., Rhea, J., Jacobsen, D., Romari, K., Smith, C., Rabenstein, J., Irigoyen, M., Clarke, M., Francis, L., Luche, M., Carr, G.J. and Mocek, U. (2009) Neopyrrolomycins with broad spectrum antibacterial activity. J. Nat. Prod., 72 (2), 276-279.
36. Tatsuta, K. and Itoh, M. (1994) Synthesis and biological evaluation of neopyrrolomycin analogs. J. Antibiot., 47 (2), 262-265.
37. Sangnoi, Y., Sakulkeo, O., Yuenyongsawad, S., Kanjana-opas, A., Ingkaninan, K., Plubrukarn, A. and Suwanborirux, K. (2008) Acetylcholinesterase-inhibiting activity of pyrrole derivatives from a novel marine gliding bacterium, Rapidithrix thailandica. Mar. Drugs, 6 (4), 578-586.
38. Rudi, A., Evan, T., Aknin, M. and Kashman, Y. (2000) Polycitone B and prepolycitrin A: two novel alkaloids from the marine ascidian Polycitor africanus. J. Nat. Prod., 63 (6), 832-833.
39. Kreipl, A.T., Reid, C. and Steglich, W. (2002) Total syntheses of the marine pyrrole alkaloids polycitone A and B. Org. Lett., 4 (19), 3287-3288.
40. Kawasaki, T., Sakurai, F. and Hayakawa, Y. (2008) A prodigiosin from the roseophilin producer Streptomyces griseoviridis. J. Nat. Prod., 71 (7), 1265-1267.
41. Clift, M.D. and Thomson, R.J. (2009) Development of a merged conjugate addition/oxidative coupling sequence. Application to the enantioselective total synthesis of metacycloprodigiosin and prodigiosin R1. J. Am. Chem. Soc., 131 (40), 14579-14583.
42. Hiort, J., Maksimenka, K., Reichert, M., Perovic-Ottstadt, S., Lin, W.H., Wray, V., Steube, K., Schaumann, K., Weber, H., Proksch, P., Ebel, R., Müller, W.E.G. and Bringmann, G. (2004) New natural products from the sponge-derived fungus Aspergillus niger. J. Nat. Prod., 67 (9), 1532-1543.
43. Ezaki, N., Shomura, T., Koyama, M., Niwa, T., Kojima, M., Inouye, S., Ito, T. and Niida, T. (1981) New chlorinated nitropyrrole antibiotics, pyrrolomycin A and B (SF-2080 A and B). J. Antibiot., 34 (10), 1363-1365.
44. Guo, Y., Li, X., Wang, J., Xu, J. and Li, N. (2005) A new alkaloid from the fruits of Celastrus orbiculatus. Fitoterapia, 76 (2), 273-275.
45. Jin, Y.P., Wei, X.N. and Shi, Y.P. (2007) Chemical constituents from Cynoglossum gansuense. Helv. Chim. Acta, 90 (4), 776-782.
46. Kato, S., Shindo, K., Kawai, H., Odagawa, A., Matsuoka, M. and Mochizuki, J. (1993) Pyrrolostatin, a novel lipid peroxidation inhibitor from Streptomyces chrestomyceticus: taxonomy, fermentation, isolation, structure elucidation and biological properties. J. Antibiot., 46 (6), 892-899.
47. Fumoto, Y., Eguchi, T., Uno, H. and Ono, N. (1999) Synthesis of pyrrolostatin and its analogues. J. Org. Chem., 64 (17), 6518-6521.
48. Kam, T.S., Subramaniam, G. and Chen, W. (1999) Alkaloids from Kopsia dasyrachis. Phytochemistry, 51 (1), 159-169.
49. Beck, E.M., Hatley, R. and Gaunt, M.J. (2008) Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy. Angew. Chem. Int. Ed., 47 (16), 3004-3007.
50. Tsuda, M., Nozawa, K., Shimbo, K. and Kobayashi, J. (2003) Rigidins B-D, new pyrrolopyrimidine alkaloids from a tunicate Cystodytes species. J. Nat. Prod., 66 (2), 292-294.
51. Gupton, J.T., Banner, E.J., Scharf, A.B., Norwood, B.K., Kanters, R.P.F., Dominey, R.N., Hempel, J.E., Kharlamova, A., Bluhn-Chertudi, I. and Hickenboth, C.R. (2006) The application of vinylogous iminium salt derivatives to an efficient synthesis of the pyrrole containing alkaloids rigidin and rigidin E. Tetrahedron, 62 (35), 8243-8255.
52. Yamagishi, Y., Matsuoka, M., Odagawa, A., Kato, S., Shindo, K. and Mochizuki, J. (1993) Rumbrin, a new cytoprotective substance produced by Auxarthron umbrinum. I. Taxonomy, production, isolation and biological activities. J. Antibiot., 46 (6), 884-887.
53. Clark, B.R. and Murphy, C.D. (2009) Biosynthesis of pyrrolylpolyenes in Auxarthron umbrinum. Org. Biomol. Chem., 7 (1), 111-116.
54. El Sayed, K.A., Hamann, M.T., Abd El-Rahman, H.A. and Zaghloul, A.M. (1998) New pyrrole alkaloids from Solanum sodomaeum. J. Nat. Prod., 61 (6), 848-850.
55. Assmann, M., Zea, S. and Köck, M. (2001) Sventrin, a new bromopyrrole alkaloid from the Caribbean sponge Agelas sventres. J. Nat. Prod., 64 (12), 1593-1595.
56. Carte, B. and Faulkner, D.J. (1983) Defensive metabolites from three nembrothid nudibranchs. J. Org. Chem., 48 (14), 2314-2318.
57. Pinkerton, D.M., Banwell, M.G. and Willis, A.C. (2007) Total syntheses of tambjamines C, E, F, G, H, I and J, BE-18591, and a related alkaloid from the marine bacterium Pseudoalteromonas tunicata. Org. Lett., 9 (24), 5127-5130.
58. Utkina, N.K., Makarchenko, A.E. and Denisenko, V.A. (2005) Zyzzyanones B-D, dipyrroloquinones from the marine sponge Zyzzya fuliginosa. J. Nat. Prod., 68 (9), 1424-1427.
59. Jolicoeur, B., Chapman, E.E., Thompson, A. and Lubell, W.D. (2006) Pyrrole protection. Tetrahedron, 62 (50), 11531-11563.
60. Hanefeld, U. and Laatsch, H. (1991) Synthesis of isopentabromopseudilin. Liebigs Ann. Chem., 865-869.
61. Morrison, M.D., Hanthorn, J.J. and Pratt, D.A. (2009) Synthesis of pyrrolnitrin and related halogenated phenylpyrroles. Org. Lett., 11 (5), 1051-1054.
62. Martin, R., Jaeger, A., Boehl, M., Richter, S., Fedorov, R., Manstein, D.J., Gutzeit, H.O. and Knölker, H.J. (2009) Total synthesis of pentabromo-and pentachloropseudilin, and synthetic analogues-allosteric inhibitors of myosin ATPase. Angew. Chem. Int. Ed., 48 (43), 8042-8046.
63. Fürstner, A., Szillat, H., Gabor, B. and Mynott, R. (1998) Platinum-and acid-catalyzed enyne metathesis reactions: mechanistic studies and applications to the syntheses of streptorubin B and metacycloprodigiosin. J. Am. Chem. Soc., 120 (33), 8305-8314.
64. Ridley, C.P., Reddy, M.V., Rocha, G., Bushman, F.D. and Faulkner, D.J. (2002) Total synthesis and evaluation of lamellarin α 20-sulfate analogues. Bioorg. Med. Chem., 10 (10), 3285-3290.
65. Ishibashi, F., Miyazaki, Y. and Iwao, M. (1997) Total syntheses of lamellarin D and H. The first synthesis of lamellarin -class marine alkaloids. Tetrahedron, 53 (17), 5951-5962.
66. Banwell, M. and Hockless, D. (1997) Convergent total synthesis of lamellarin K. Chem. Commun., (23), 2259-2260.
67. Heim, A., Terpin, A. and Steglich, W. (1997) Biomimetic synthesis of lamellarin G trimethyl ether. Angew. Chem. Int. Ed., 36 (1/2), 155-156.
68. Gupton, J.T., Miller, R.B., Krumpe, K.E., Clough, S.C., Banner, E.J., Kanters, R.P.F., Du, K.X., Keertikar, K.M., Lauerman, N.E. and Solano, J.M. (2005) The application of vinylogous iminium salt derivatives to an efficient relay synthesis of the pyrrole containing alkaloids polycitone A and B. Tetrahedron, 61 (7), 1845-1854.
69. Handy, S.T., Zhang, Y. and Bregman, H. (2004) A modular synthesis of the lamellarins: total synthesis of lamellarin G trimethyl ether. J. Org. Chem., 69 (7), 2362-2366.
70. Weinreb, S.M. (2007) Some recent advances in the synthesis of polycyclic imidazole-containing marine natural products. N at. Prod. Rep., 24 (5), 931-948.
71. Forte, B., Malgesini, B., Piutti, C., Quartieri, F., Scolaro, A. and Papeo, G. (2009) A submarine journey. The pyrrole-imidazole alkaloids. Mar. Drugs, 7 (4), 705-753.
72. Birman, V.B. and Jiang, X.T. (2004) Synthesis of sceptrin alkaloids. Org. Lett., 6 (14), 2369-2371.
73. Su, S., Seiple, I.B., Young, I.S. and Baran, P.S. (2008) Total syntheses of (±)-massadine and massadine chloride. J. Am. Chem. Soc., 130 (49), 16490-16491.
74. Ando, N. and Terashima, S. (2006) A novel synthesis of the 2-aminoimidazol -4-carbaldehyde derivatives, versatile synthetic intermediates for 2-aminoimidazole alkaloids. Synlett, (17), 2836-2840.
75. Meketa, M.L. and Weinreb, S.M. (2007) A new total synthesis of the zinc matrixmetalloproteinase inhibitor ageladine a featuring a biogenetically patterned 6 π-2-azatriene electrocyclization. O rg. Lett., 9 (5), 853-855.
76. Bhandari, M.R., Sivappa, R. and Lovely, C.J. (2009) Total synthesis of the putative structure of nagelamide D. Org. Lett., 11 (7), 1535-1538.
77. Zoellinger, M., Mayer, P. and Lindel, T. (2007) Enantioselective total synthesis of (-)-dibromophakellstatin. Synlett, (17), 2756-2758.
78. Papeo, G., Gomez-Zurita, M.A., Borghi, D. and Varasi, M. (2005) Total synthesis of ({dot plus})-cyclooroidin. Tetrahedron Lett., 46 (50), 8635-8638.
79. Hama, N., Matsuda, T., Sato, T. and Chida, N. (2009) Total synthesis of (-)-agelastatin A: the application of a sequential sigmatropic rearrangement. Org. Lett., 11 (12), 2687-2690
80. Domostoj, M.M., Irving, E., Scheinmann, F. and Hale, K.J. (2004) New total synthesis of the marine antitumor alkaloid (-)-agelastatin A. Org. Lett., 6 (15), 2615-2618.
81. Feldman, K.S. and Skoumbourdis, A.P. (2005) Extending Pummerer reaction chemistry. Synthesis of (±)-dibromophakellstatin by oxidative cyclization of an imidazole derivative. Org. Lett., 7 (5), 929-931.
82. Trost, B.M. and Dong, G. (2006) New class of nucleophiles for palladium -catalyzed asymmetric allylic alkylation. Total synthesis of agelastatin A. J. Am. Chem. Soc., 128 (18), 6054-6055.
83. Trost, B.M. and Dong, G.B. (2009) A stereodivergent strategy to both product enantiomers from the same enantiomer of a stereoinducing catalyst: agelastatin A. Chem. Eur. J., 15 (28), 6910-6919.
84. Wu, J., Vetter, W., Gribble, G.W., Schneekloth, J.S. Jr., Blank, D.H. and Gorls, H. (2002) Structure and synthesis of the natural heptachloro-1' -methyl-1,2'-bipyrrole (Q1). Angew. Chem. Int. Ed., 41 (10), 1740-1743.
85. Fürstner, A. (2003) Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years. Angew. Chem. Int. Ed., 42 (31), 3582-3603.
86. Boger, D.L. and Patel, M. (1988) Total synthesis of prodigiosin, prodigiosene, and desmethoxyprodigiosin: Diels-Alder reactions of heterocyclic azadienes and development of an effective palladium(II)-promoted 2,2'-bipyrrole coupling procedure. J. Org. Chem., 53 (7), 1405-1415.
87. Reeves, J.T., Song, J.J., Tan, Z., Lee, H., Yee, N.K. and Senanayake, C.H. (2007) A general synthesis of substituted formylpyrroles from ketones and 4-formyloxazole. Org. Lett., 9 (10), 1875-1878.
88. Reeves, J.T. (2007) A concise synthesis of butylcycloheptylprodigiosin. Org. Lett., 9 (10), 1879-1881.
89. Fürstner, A. and Weintritt, H. (1998) Total synthesis of roseophilin. J. Am. Chem. Soc., 120 (12), 2817-2825.
90. Donohoe, T.J. and Thomas, R.E. (2007) Partial reduction of pyrroles: application to natural product synthesis. Chem. Rec., 7 (3), 180-190.
91. Amos, R.I.J., Gourlay, B.S., Molesworth, P.P., Smith, J.A. and Sprod, O.R. (2005) Annulation of pyrrole: application to the synthesis of indolizidine alkaloids. Tetrahedron, 61 (34), 8226-8230.
92. Donohoe, T.J. and Sintim, H.O. (2004) A concise total synthesis of (±)-1-epiaustraline. Org. Lett., 6 (12), 2003-2006.
93. Donohoe, T.J., Sintim, H.O. and Hollinshead, J. (2005) A noncarbohydrate based approach to polyhydroxylated pyrrolidizines: total syntheses of the natural products hyacinthacine A1 and 1-epiaustraline. J. Org. Chem., 70 (18), 7297-7304.
94. Robins, D.J. and Sakdarat, S. (1979) Synthesis of the 8 β-pyrrolizidine bases (+)-isoretronecanol, (+)-laburnine, and (+)-supinidine. J. Chem. Soc. Chem. Commun., (24), 1181-1182.
95. Giblin, G.M.P., Jones, C.D. and Simpkins, N.S. (1998) The total synthesis of the analgesic alkaloid epibatidine. J. Chem. Soc. Perkin Trans. I, (22), 3689-3698.
96. Berini, C., Pelloux-Leon, N., Minassian, F. and Denis, J.N. (2009) From N-triisopropylsilylpyrrole to an optically active C-4 substituted pyroglutamic acid: total synthesis of penmacric acid. Org. Biomol. Chem., 7 (21), 4512-4516.
97. Terpin, A., Polborn, K. and Steglich, W. (1995) Biomimetic total synthesis of polycitrin A. Tetrahedron, 51 (36), 9941-9946.
98. Boger, D.L. and Baldino, C.M. (1993) d,l-and meso-Isochrysohermidin: total synthesis and interstrand DNA crosslinking. J. Am. Chem. Soc., 115 (24), 11418-11425.
99. Scott, M.S., Luckhurst, C.A. and Dixon, D.J. (2005) A total synthesis of tarchonanthuslactone exploiting N-pyrrole carbinols as efficient stereocontrolling elements. Org. Lett., 7 (26), 5813-5816.
100. Pahadi, N.K., Paley, M., Jana, R., Waetzig, S.R. and Tunge, J.A. (2009) Formation of N-alkylpyrroles via intermolecular redox amination. J. Am. Chem. Soc., 131 (46), 16626-16627.
101. Hertiani, T., Edrada-Ebel, R., Ortlepp, S., van Soest, R.W.M., de Voogd, N.J., Wray, V., Hentschel, U., Kozytska, S., Mueller, W.E.G. and Proksch, P. (2010) From anti-fouling to biofilm inhibition: new cytotoxic secondary metabolites from two Indonesian agelas sponges. B ioorg. Med. Chem., 18 (3), 1297-1311.
102. Kwon, H.C., Espindola, A.P.D.M., Park, J.S., Davo-Prieto, A., Rose, M., Jensen, P.R. and Fenical, W. J. (2010) Nitropyrrolins A-E, cytotoxic farnesyl-α-nitropyrroles from a marine-derived bacterium within the actinomycete family Streptomycetaceae. J. Nat. Prod., 73, 2047-2052.
103. Raju, R, Piggott, A.M., Diaz, L.X.B., Khalil, Z. and Capon, R.J. (2010) Heronapyrroles A-C: farnesylated 2-nitropyrroles from an Australian marine-derived Streptomyces sp. Org. Lett., 12 (22), 5158-5161.
104. Guella, G., Frassanito, R., Mancini, I., Sandron, T., Modeo, L., Verni, F., Dini, F. and Petroni, G. (2010) Keronopsamides, a new class of pigments from marine ciliates. Eur. J. Org. Chem., (3) 427-434.
105. Li, Q., Jiang, J., Fan, A., Cu, Y. and Jia, Y. (2011) Total synthesis of lamellarins D, H, and R and ningalin B. Org. Lett., 13 (2), 312-315.