RSS-Feed abonnieren
DOI: 10.1055/s-0034-1378774
Synthesis of Secondary Metabolites from Higher Fungi
Publikationsverlauf
Received: 11. März 2015
Accepted after revision: 12. Mai 2015
Publikationsdatum:
09. September 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201519/lookinside/thumbnails/ss-2015-e0156-r_10-1055_s-0034-1378774-1.jpg)
Dedicated to Professor Horst Kessler on the occasion of his 75th birthday.
Abstract
Higher fungi are a promising source of new bioactive natural products with great structural diversity, ranging from polyketides to terpenoids and alkaloids. Many of these structures are a challenge for synthetic organic chemists who have been inspired to develop new total syntheses. Nevertheless, reviews covering syntheses of fungal natural products are lacking. One aim of this review is to close this gap and to present a selection of more recent syntheses of fungal secondary metabolites from different structural classes. Secondly, this review intends to demonstrate that there are many more motivations for the synthesis of natural products than to confirm a proposed structure or to report the first total synthesis of a new natural product. Thirdly, this review is intended to stimulate the interest of organic chemists in the synthesis of fungal natural products.
1 History and Importance of (Fungal) Secondary Metabolites
2 Reasons for the Synthesis of Fungal Natural Products
3 Total Syntheses of Selected Fungal Natural Products
3.1 Terpenes
3.1.1 Sesquiterpenes
3.1.1.1 Polyquinanes
3.1.1.2 Drimanes
3.1.2 Diterpenes: Cyathanes
3.1.3 Terpenes Containing a Butenolide Moiety
3.2 Alkaloids
3.3 Natural Products Derived from the Shikimate Pathway
3.3.1 Pulvinic Acid Derivatives and Terphenyl Quinones
3.3.2 Shikimate Pathway Derived Macrolides
3.3.3 Strobilurins
3.4 Aromatic Polyketides
3.4.1 Quinones
3.4.2 Resorcylates and Catechols
3.5 Sugar Derivatives
4 Conclusion and Outlook
-
References
- 1 Sertürner F. Ann. Phys. 1817; 55: 56
- 2a Achan J, Talisuna AO, Erhart A, Yeka A, Tibenderana JK, Baliraine FN, Rosenthal PJ, D’Alessandro U. Malar. J. 2011; 10: 1
- 2b Kalotka-Kreglewska H. Cent. Eur. J. Immunol. 2011; 36: 100
- 2c Woodrow CJ, Haynes RK, Krishna S. Postgrad. Med. J. 2005; 81: 71
- 3 Woodward RB, Cava MP, Ollis WD, Hunger A, Daeniker HU, Schenker K. J. Am. Chem. Soc. 1954; 76: 4749
- 4 Woodward RB. Pure Appl. Chem. 1973; 33: 145
- 5 Suh EM, Kishi Y. J. Am. Chem. Soc. 1994; 116: 11205
- 6 Chemical Library Design . Zhou JZ. Springer-Verlag; New York: 2010
- 7 Breinbauer R, Vetter IR, Waldmann H. Angew. Chem. Int. Ed. 2002; 41: 2878
- 8a Thomas GL, Johannes CW. Curr. Opin. Chem. Biol. 2011; 15: 516
- 8b Boldi AM. Curr. Opin. Chem. Biol. 2004; 8: 281
- 9 Von Hattum H, Waldmann H. J. Am. Chem. Soc. 2014; 136: 11853
- 10a Kennedy J. Nat. Prod. Rep. 2008; 25: 25
- 10b Kirschning A, Taft F, Knobloch T. Org. Biomol. Chem. 2007; 5: 3245
- 11 Newman DJ, Cragg GM. J. Nat. Prod. 2012; 75: 311
- 12 Blackwell M. Am. J. Bot. 2011; 98: 426
- 13 Beekman AM, Barrow RA. Aust. J. Chem. 2014; 67: 827
- 14 Henningsen M. Chem. Unserer Zeit 2003; 37: 98
- 15 Weber W, Anke T, Bross M, Steglich W. Planta Med. 1990; 56: 446
- 16 Nicholas GM, Blunt JW, Cole AL. J, Munro MH. G. Tetrahedron Lett. 1997; 38: 7465
- 17a Fredenhagen A, Kuhn A, Peter HH, Cuomo V, Giuliano U. J. Antibiot. 1990; 43: 655
- 17b Fredenhagen A, Hug P, Peter HH. J. Antibiot. 1990; 43: 661
- 18 Hellwig V, Dasenbrock J, Klostermeyer D, Kroiß S, Sindlinger T, Spiteller P, Steffan B, Steglich W, Engler-Lohr M, Semar S, Anke T. Tetrahedron 1999; 55: 10101
- 19 Kroiß S, Steglich W. Tetrahedron 2004; 60: 4921; for precursor molecules, see ref. 17
- 20 Lin DW, Masuda T, Biskup MB, Nelson JD, Baran PS. J. Org. Chem. 2011; 76: 1013
- 21 Peters S, Spiteller P. Eur. J. Org. Chem. 2007; 1571
- 22 Ingerl A, Justus K, Hellwig V, Steglich W. Tetrahedron 2007; 63: 6548
- 23 Konno K, Shirahama H, Matsumoto T. Tetrahedron Lett. 1983; 24: 939
- 24 Nakagawa H, Sugahara T, Ogasawara K. Tetrahedron Lett. 2001; 42: 4523
- 25 Ouchi H, Asahina A, Asakawa T, Inai M, Hamashima Y, Kan T. Org. Lett. 2014; 16: 1980
- 26 Sauter H, Steglich W, Anke T. Angew. Chem. Int. Ed. 1999; 38: 1328
- 27 Keller NP, Turner G, Bennett JW. Nat. Rev. Microbiol. 2005; 3: 937
- 28a Poulton JE. Plant Physiol. 1990; 94: 401
- 28b Vetter J. Toxicon 2000; 38: 11
- 28c Zagrobelny M, Bak S, Møller BL. Phytochemistry 2008; 69: 1457
- 29 Caspar J, Spiteller P. ChemBioChem 2015; 16: 570
- 30 Kindler BL. J, Spiteller P. Angew. Chem. Int. Ed. 2007; 46: 8076
- 31 Lang M, Mühlbauer A, Jägers E, Steglich W. Eur. J. Org. Chem. 2008; 3544
- 32 Banwell MG, Austin KA. B, Willis AC. Tetrahedron 2007; 63: 6388
- 33 Reekie TA, Austin KA. B, Banwell MG, Willis AC. Aust. J. Chem. 2008; 61: 94
- 34a Bon DJ.-Y. D, Banwell MG, Willis AC. Tetrahedron 2010; 66: 7807
- 34b Bon DJ.-Y. D, Banwell MG, Cade IA, Willis AC. Tetrahedron 2011; 67: 8348
- 35 King T, Farrell K, Halsall T, Thaller V. J. Chem. Soc., Chem. Commun. 1977; 727
- 36 Mihelcic J, Moeller KD. J. Am. Chem. Soc. 2004; 126: 9106
- 37 Takeuchi T, Iinuma H, Momose I, Matsui S. Jpn. Kokai Tokkyo Koho JP 2001-9452 20010117, 2002
- 38 Kögl M, Brecker L, Warrass R, Mulzer J. Eur. J. Org. Chem. 2008; 2714
- 39 Abraham WR, Hanssen HP, Urbasch I. Z. Naturforsch., C: J. Biosci. 1991; 46: 169
- 40a Stadler M, Anke H, Sterner O. J. Antibiot. 1994; 47: 1284
- 40b Stadler M, Anke H, Sterner O. Tetrahedron 1994; 50: 12649
- 41 Takao K, Hara M, Tsujita T, Yoshida K, Tadano K. Tetrahedron Lett. 2001; 42: 4665
- 42 Brocksom TJ, Zanotto PR, Brocksom U. Tetrahedron Lett. 2005; 46: 2397
- 43 Ayer WA, Cruz ER. J. Org. Chem. 1993; 58: 7529
-
44 Ashfeld BL, Martin SF. Tetrahedron 2006; 62: 10497
- 45 Anderson JR, Edwards RL, Freer AA, Mabelis RP, Poyser JP, Spencer H, Whalley AJ. S. J. Chem. Soc., Chem. Commun. 1984; 917
- 46 Fleck M, Bach T. Angew. Chem. Int. Ed. 2008; 47: 6189
- 47 Bassett C, Underwood RT, Kepler JA, Hamilton PB. Phytopathology 1967; 57: 1046
- 48a Paquette LA, Peng X, Yang J. Angew. Chem. Int. Ed. 2007; 46: 7817
- 48b Paquette LA, Peng X, Yang J, Kang H. J. Org. Chem. 2008; 73: 4548
- 49 Bollinger P. 1965, as reported in 1971; see: Thomson RH. Naturally Occurring Quinones . Academic Press; New York: 1971: 131
- 50 Srikrishna A, Vasantha LakshmiB, Ravikumar PC. Tetrahedron Lett. 2006; 47: 1277
- 51 Kajimoto T, Yamashita M, Imamura Y, Nohara T, Shibata M. Chem. Lett. 1989; 527
- 52a Srikrishna A, Ravikumar PC. Tetrahedron Lett. 2005; 46: 6105
-
52b Srikrishna A, Ravikumar PC. Tetrahedron 2006; 62: 9393
- 53 Magnusson G, Thoren S, Wickberg B. Tetrahedron Lett. 1972; 1105
- 54 Bell RP. L, Wijnberg JB. P. A, de Groot A. J. Org. Chem. 2001; 66: 2350
- 55 Johansson M, Aujard I, Röme D, Anke H, Sterner O. Z. Naturforsch., B: J. Chem. Sci. 2005; 60: 984
- 56 Heatley NG, Jennings MA, Florey HW. Br. J. Exp. Pathol. 1947; 28: 35
- 57 Mellows G, Mantle PG, Feline TC, Williams DJ. Phytochemistry 1973; 12: 2717
- 58 Yuan C, Jiao L, Yu Z.-X. Tetrahedron Lett. 2010; 51: 5674
- 59 Singh V, Tosha DK, Mobin SM. Tetrahedron Lett. 2004; 45: 1729
- 60 Singh V, Pal S, Tosha DK, Mobin SM. Tetrahedron 2007; 63: 2446
- 61 Stadler M, Anke T, Dasenbrock J, Steglich W. Z. Naturforsch., C: J. Biosci. 1993; 48: 545
- 62 Kupka J, Anke T, Giannetti BM, Steglich W. Arch. Microbiol. 1981; 130: 223
- 63 Paquette LA, Geng F. J. Am. Chem. Soc. 2002; 124: 9199
- 64 Takeuchi T, Iinuma H, Iwanaga J, Takahashi H, Umezawa H. J. Antibiot. 1969; 22: 215
- 65 Singh V, Samantaa B, Kaneb VV. Tetrahedron 2000; 56: 7785
- 66 Mehta G, Murthy AS. K. Tetrahedron Lett. 2003; 44: 5243
- 67 Rukachaisirikul V, Tansakul C, Saithong S, Pakawatchai C, Isaka M, Suvannakad R. J. Nat. Prod. 2005; 68: 1674
- 68 Hanssen H.-P, Abraham W.-R. Tetrahedron 1988; 44: 2175
- 69 Anke T, Heim J, Knoch F, Mocek U, Steffan B, Steglich W. Angew. Chem., Int. Ed. Engl. 1985; 24: 709
- 70 Chen P, Carroll PJ, Sieburth SM. Org. Lett. 2010; 12: 4510
- 71 Hashimoto T, Tori M, Mizuno Y, Asakawa Y. Tetrahedron Lett. 1987; 28: 6303
- 72 Tori M, Hamada N, Sono M, Sono Y, Ishikawa M, Nakashima K, Hashimoto T, Asakawa Y. Tetrahedron Lett. 2000; 41: 3099
- 73 Erkel G, Lorenzen K, Anke T, Velten R, Gimenez A, Steglich W. Z. Naturforsch., C: J. Biosci. 1995; 50: 1
- 74 Jauch J. Angew. Chem. Int. Ed. 2000; 39: 2764
- 75 Wallner C, Jauch J. Synthesis 2004; 665
- 76 Chiang H.-C, Wu D.-P, Cherng I.-W, Ueng C.-H. Phytochemistry 1995; 39: 613
- 77a Ayer WA, Craw PA, Stout TJ, Clardy J. Can. J. Chem. 1989; 67: 7738
- 77b Ayer WA, Craw PA. Can. J. Chem. 1989; 67: 1371
-
78 Shi H, Fang L, Tan C, Shi L, Zhang W, Li C.-C, Luo T, Yang Z. J. Am. Chem. Soc. 2011; 133: 14944
- 79a Allbutt AD, Ayer WA, Brodie HJ, Johri BN, Taube H. Can. J. Microbiol. 1971; 17: 1401
- 79b Ayer WA, Taube H. Tetrahedron Lett. 1972; 1917
- 79c Ayer WA, Taube H. Can. J. Chem. 1973; 51: 3842
- 79d Ayer WA, Nakashima TT, Ward DE. Can. J. Chem. 1978; 56: 2197
- 79e Ayer WA, Carstens LL. Can. J. Chem. 1973; 51: 3157
- 79f Ayer WA, Browne LM, Mercer JR, Taylor DR, Ward DE. Can. J. Chem. 1978; 56: 717
- 79g Ayer WA, Yoshida T, van Schie DM. J. Can. J. Chem. 1978; 56: 2113
- 80 Ward DE, Shen J. Org. Lett. 2007; 9: 2843
- 81 Kim K, Cha JK. Angew. Chem. Int. Ed. 2009; 48: 5334
- 82 Shibata H, Tokunaga T, Karasawa D, Hirota A, Nakayama M, Nozaki H, Tada T. Agric. Biol. Chem. 1989; 53: 3373
- 83 Piers E, Gilbert M, Cook KL. Org. Lett. 2000; 2: 1407
- 84 Kita T, Takaya Y, Oshima Y, Ohta T, Aizawa K, Hirano T, Inakuma T. Tetrahedron 1998; 54: 11877
- 85 Waters SP, Tian Y, Li Y.-M, Danishefsky SJ. J. Am. Chem. Soc. 2005; 127: 13514
- 86 Kanoh N, Sakanishi K, Iimori E, Nishimura K, Iwabuchi Y. Org. Lett. 2011; 13: 2864
- 87 Kawagishi H, Shimada A, Shirai R, Okamoto K, Ojima F, Sakamoto H, Ishiguro Y, Furukawa S. Tetrahedron Lett. 1994; 35: 1569
- 88 Kawagishi H, Shimada A, Hosokawa S, Mori H, Sakamoto H, Ishiguro Y, Sakemi S, Bordner J, Kojima N, Furukawa S. Tetrahedron Lett. 1996; 37: 7399
- 89 Watanabe H, Takano M, Umino A, Ito T, Ishikawa H, Nakada M. Org. Lett. 2007; 9: 359
- 90 Watanabe H, Nakada M. J. Am. Chem. Soc. 2008; 130: 1150
- 91 Kawagishi H, Akachi T, Ogawa T, Masuda K, Yamaguchi K, Yazawa K, Takahashi M. Heterocycles 2006; 69: 253
- 92 Yajima A, Kagohara Y, Shikai K, Katsuta R, Nukada T. Tetrahedron 2012; 68: 1729
- 93 Arnone A, Cardillo R, Meille SV, Nasini G, Tollazi M. J. Chem. Soc., Perkin Trans. 1 1994; 2165
-
94 Larrosa I, Da Silva MI, Gomez PM, Hannen P, Ko E, Lenger SR, Linke SR, White AJ. P, Wilton D, Barrett AG. M. J. Am. Chem. Soc. 2006; 128: 14042
- 95 Anchel M, Harvey A, Robins WJ. Proc. Natl. Acad. Sci. U.S.A. 1952; 38: 927
- 96 Teske JA, Deiters A. J. Org. Chem. 2008; 73: 342
- 97 Antkowiak WZ, Gessner WP. Tetrahedron Lett. 1979; 1931
- 98 Mongin F, Trécourt F, Mongin O, Quéguiner G. Tetrahedron 2002; 58: 309
- 99 Guengerich FP, DiMari SJ, Broquist HP. J. Am. Chem. Soc. 1973; 95: 2055
- 100a Punniyamurthy T, Irie R, Katsuki T. Chirality 2000; 12: 464
- 100b De Vicente J, Arrayas RG, Canada J, Carretero JC. Synlett 2000; 53
- 100c Lindsay KB, Pyne SG. J. Org. Chem. 2002; 67: 7774
- 100d Lindsay KB, Pyne SG. Aust. J. Chem. 2004; 57: 669
- 100e Martin R, Murruzzu C, Pericas MA, Riera A. J. Org. Chem. 2005; 70: 2325
- 100f Heimgaertner G, Raatz D, Reiser O. Tetrahedron 2005; 61: 643
- 100g Ceccon J, Greene AE, Poisson J.-F. Org. Lett. 2006; 8: 4739
- 100h Guo H, O’Doherty GA. Org. Lett. 2006; 8: 1609
- 100i Au CW. G, Pyne SG. J. Org. Chem. 2006; 71: 7097
- 100j Dechamps I, Pardo DG, Cossy J. Tetrahedron 2007; 63: 9082
- 100k Guo H, O’Doherty GA. Tetrahedron 2008; 64: 304
- 100l Alam MA, Kumar A, Vankar YD. Eur. J. Org. Chem. 2008; 4972
- 100m Shi G.-F, Li J.-Q, Jiang X.-P, Cheng Y. Tetrahedron 2008; 64: 5005
- 100n Sharma PK, Shah RN, Carver JP. Org. Process Res. Dev. 2008; 12: 831
- 100o Hakansson AE, van Ameijde J, Horne G, Nash RJ, Wormald MR, Kato A, Besra GS, Gurcha S, Fleet GW. J. Tetrahedron Lett. 2008; 49: 179
- 100p Tian Y.-S, Joo J.-E, Kong B.-S, Pham V.-T, Lee K.-Y, Ham W.-H. J. Org. Chem. 2009; 74: 3962
- 100q Choi H.-G, Kwon J.-H, Kim J.-C, Lee W.-K, Eum H.-S, Ha H.-J. Tetrahedron Lett. 2010; 51: 3284
- 100r Chooprayoon S, Kuhakarn C, Tuchinda P, Reutrakul V, Pohmakotr M. Org. Biomol. Chem. 2011; 9: 531
- 100s Chen M.-J, Tsai Y.-M. Tetrahedron 2011; 67: 1564
- 100t Murthy SN, Nageswar YV. D. Synthesis 2011; 755
- 100u Archibald G, Lin C.-P, Boyd P, Barker D, Caprio V. J. Org. Chem. 2012; 77: 7968
- 100v Dhand V, Draper JA, Moore J, Britton R. Org. Lett. 2013; 15: 1914
- 100w Li QR, Dong GR, Park SJ, Hong YR, Kim IS, Jung YH. Eur. J. Org. Chem. 2013; 4427
-
101 Buschmann N, Rueckert A, Blechert S. J. Org. Chem. 2002; 67: 4325
-
102 Bates RW, Dewey MR. Org. Lett. 2009; 11: 3706
- 103 Bates RW, Dewey MR, Tang CH, Safii S, Hong Y, Hsieh JK. H, Siah PS. Synlett 2011; 2053
- 104 Kwon HY, Park CM, Lee SB, Youn J.-H, Kang SH. Chem. Eur. J. 2008; 14: 1023
- 105 Oxenford SJ, Moore SP, Carbone G, Barker G, O’Brien P, Shipton MR, Gilday J, Campos KR. Tetrahedron: Asymmetry 2010; 21: 1563
- 106 Louvel J, Chemla F, Demont E, Ferreira F, Perez-Luna A. Org. Lett. 2011; 13: 6452
- 107 Wardrop DJ, Bowen EG. Org. Lett. 2011; 13: 2376
- 109 Schmiedeberg O, Koppe R. Das Muscarin, das giftige Alkaloid des Fliegenpilzes (Agaricus muscarius L.), seine Darstellung, chemischen Eigenschaften, physiologischen Wirkungen, toxicologische Bedeutung und sein Verhältniss zur Pilzvergiftung im allgemeinen. Verlag von F. C. W. Vogel; Leipzig: 1869
- 110 Popsavin V, Berić O, Popsavin M, Radić L, Csanádi Ćirin-NovtaV. Tetrahedron 2000; 56: 5929
- 111 Kang KH, Cha MY, Pae AN, Choi KI, Cho YS, Koh HY, Chung BJ. Tetrahedron Lett. 2000; 41: 8137
- 112 Knight DW, Staples ER. Tetrahedron Lett. 2002; 43: 6771
- 113 Hartung J, Kneuer R. Tetrahedron: Asymmetry 2003; 14: 3019
- 114 Knight DW, Shaw DE, Staples ER. Eur. J. Org. Chem. 2004; 1973
- 115 Boukouvalas J, Radu I.-I. Tetrahedron Lett. 2007; 48: 2971
- 116 Ahmed Z, Langer P. Tetrahedron 2005; 61: 2055
- 117 Bernier D, Moser F, Brückner R. Synthesis 2007; 2240
- 118 Bernier D, Brückner R. Synthesis 2007; 2249
- 119 Nadal B, Rouleau J, Besnard H, Thuéry P, Le Gall T. Tetrahedron 2011; 67: 2605
- 120 Xu H.-W, Xu C, Fan Z.-Q, Zhao L.-J, Liu H.-M. Bioorg. Med. Chem. Lett. 2013; 23: 737
- 121 Besl H, Bresinsky A, Kilpert C, Marschner W, Schmidt HM, Steglich W. Z. Naturforsch., B: J. Chem. Sci. 2008; 63: 887
- 122 Geraci C, Neri P, Paternò C, Rocco C, Tringali C. J. Nat. Prod. 2000; 63: 347
- 123 Justus K, Herrmann R, Klamann J.-D, Gruber G, Hellwig V, Ingerl A, Polborn K, Steffan B, Steglich W. Eur. J. Org. Chem. 2007; 5560
- 124 Anke T, Oberwinkler F, Steglich W, Schramm G. J. Antibiot. 1977; 30: 806
- 125 Coleman RS, Lu X. Chem. Commun. 2006; 423
- 126 Daferner M, Anke T, Hellwig V, Steglich W, Sterner O. J. Antibiot. 1998; 51: 816
- 127 Buchanan MS, Steglich W, Anke T. Z. Naturforsch., C: J. Biosci. 1999; 54: 463
- 128 Zapf S, Werle A, Anke T, Klostermeyer D, Steffan B, Steglich W. Angew. Chem., Int. Ed. Engl. 1995; 34: 196
- 129 Uchiro H, Nagasawa K, Aiba Y, Kobayashi S. Tetrahedron Lett. 2000; 41: 4165
- 130 Uchiro H, Nagasawa K, Aiba Y, Kotake T, Hasegawa D, Kobayashi S. Tetrahedron Lett. 2001; 42: 4531
- 131 Engler M, Anke T, Klostermeyer D, Steglich W. J. Antibiot. 1995; 48: 884
- 132 Brooke DG, Morris JC. Tetrahedron Lett. 2008; 49: 2414
- 133 Gill M, Smrdel AF, Strauch RJ, Begley MJ. J. Chem. Soc., Perkin Trans. 1 1990; 1583
- 134 Elsworth C, Gill M, Ten A. Aust. J. Chem. 1999; 52: 1115
- 135 Elsworth C, Gill M, Raudies E, Ten A. Aust. J. Chem. 2000; 53: 41
- 136 Gill M, Steglich W. Progress in the Chemistry of Organic Natural Products . Vol. 51. Springer; New York: 1987: 242
- 137 Fugmann B, Arnold S, Steglich W, Fleischhauer J, Repges C, Koslowski A, Raabe G. Eur. J. Org. Chem. 2001; 3097
- 138 Spiteller P, Steglich W. J. Nat. Prod. 2002; 65: 725
- 139 Omoloa JO, Anke H, Sterner O. Phytochemistry 2002; 60: 431
- 140 Arnone A, Carduo R, Nasini G, Vajna de Pava O. J. Nat. Prod. 1994; 57: 602
- 141 Kobayashi S, Ando A, Kuroda H, Ejima S, Masuyama A, Ryu I. Tetrahedron 2011; 67: 9087
- 142 Ueda K, Tsujimori M, Kodani S, Chiba A, Kubo M, Masuno K, Sekiya A, Nagai K, Kawagishi H. Bioorg. Med. Chem. 2008; 16: 9467
- 143 Zechlin L, Wolf M, Steglich W, Anke T. Liebigs Ann. Chem. 1981; 2099
- 144 Fürstner A, Gastner T. Org. Lett. 2000; 2: 2467
- 145 Ito-Kobayashi M, Aoyagi A, Tanaka I, Muramatsu Y, Umetani M, Takatsu T. J. Antibiot. 2008; 61: 128
- 146 Shinozuka T, Yamamoto Y, Hasegawa T, Saito K, Naito S. Tetrahedron Lett. 2008; 49: 1619
- 147 Cordes J, Calo F, Anderson K, Pfaffeneder T, Laclef S, White AJ. P, Barrett AG. M. J. Org. Chem. 2012; 77: 652
- 148 Hellwig V, Dasenbrock J, Gräf C, Kahner L, Schumann S, Steglich W. Eur. J. Org. Chem. 2002; 2895
- 149 Ebel H, Polborn K, Steglich W. Eur. J. Org. Chem. 2002; 2905
- 150 Ebel H, Knör S, Steglich W. Tetrahedron 2003; 59: 123
- 151a Atsumi S, Umezawa K, Iinuma H, Naganawa H, Nakamura H, Iitaka Y, Takeuchi T. J. Antibiot. 1990; 43: 49
- 151b Atsumi S, Iinuma H, Nosaka C, Umezawa K. J. Antibiot. 1990; 43: 1579
- 152 Hansen FG, Bundgaard E, Madsen R. J. Org. Chem. 2005; 70: 10139
- 153 Kireev AS, Breithaupt AT, Collins W, Nadein ON, Kornienko A. J. Org. Chem. 2005; 70: 742
- 154 Ding J.-H, Feng T, Li Z.-H, Yang X.-Y, Guo H, Yin X, Wang G.-Q, Liu J.-K. Org. Lett. 2012; 14: 4976
- 155 Yang X.-Y, Feng T, Li Z.-H, Sheng Y, Yin X, Leng Y, Liu J.-K. Org. Lett. 2012; 14: 5382
- 156 Wang Y, Wang S.-J, Mo S.-Y, Li S, Yang Y.-C, Shi J.-G. Org. Lett. 2005; 7: 4733
- 157 Winner M, Giménez A, Schmidt H, Sontag B, Steffan B, Steglich W. Angew. Chem. Int. Ed. 2004; 43: 1883
- 158a Evidente A, Kornienko A, Cimmino A, Andolfi A, Lefranc F, Mathieu V, Kiss R. Nat. Prod. Rep. 2014; 31: 617
- 158b Song F, Wu S.-H, Zhai Y.-Z, Xuan Q.-C, Wang T. Chem. Biodiversity 2014; 11: 673
- 158c Rateb ME, Ebel R. Nat. Prod. Rep. 2011; 28: 290
- 158d Ebel R. Mar. Drugs 2010; 8: 2340
- 158e Molnár I, Gibson DM, Krasnoff SB. Nat. Prod. Rep. 2010; 27: 1241
- 158f Geris R, Simpson TJ. Nat. Prod. Rep. 2009; 26: 1063
- 158g Saleem M, Ali MS, Hussain S, Jabbar A, Ashraf M, Lee YS. Nat. Prod. Rep. 2007; 24: 1142
- 159 Li E, Zang F, Niu S, Liu X, Liu G, Che Y. Org. Lett. 2012; 14: 3320
- 160 Lin Z, Koch M, Aziz MH. A, Galindo-Murillo R, Tianero MD, Cheatham TE, Barrows LR, Reilly CA, Schmidt EW. Org. Lett. 2014; 16: 4774