Assembly of the Nosiheptide A-Ring: A Fruitful Lesson

Abstract

The synthesis of a 28-membered thiopeptide macrocycle is described. Key steps are mild aza-Wittig thiazole ring closures, a scandium(III)-mediated regioselective ester hydrolysis, and a highly efficient macrolactam formation with its 3-hydroxypyridine nucleus orthogonally protected.

Key words

antibiotics - aza-Wittig reaction - heterocycles - natural products - macrocyclization - thiopeptides.

• References

• 1 Author’s present address: ChemRoutes Corporation, 9719-42 Ave., Edmonton, Alberta, T6E 5P8, Canada.
• 2 Author’s present address: BayerCropScience, Alfred-Nobel-Str. 50, 40789 Monheim, Germany.
• 3a Rhone-Poulenc SA. FR 1392453, 1961
• 3b Benazet F, Cartier M, Florent J, Godard C, Jung G, Lunel J, Mancy D, Pascal C, Renaut J, Tarridec P, Theilleux J, Tissier R, Dubost M, Ninet L. Experientia 1980; 36: 414
• 4 Bagley MC, Dale JW, Merritt EA, Xiong X. Chem. Rev. 2005; 105: 685

Reviews:
• 5a Hughes RA, Moody CJ. Angew. Chem. Int. Ed. 2007; 46: 7930
• 5b Nicolaou KC, Chen JS, Edmonds DJ, Estrada AA. Angew. Chem. Int. Ed. 2009; 48: 660
• 6 Haste NM, Thienphrapa W, Tran DN, Lösgen S, Sun P, Nam SJ, Jensen PR, Fenical W, Sakoulas G, Nizet V, Hensler ME. J. Antibiot. 2012; 65: 593
• 7a Harms JM, Wilson DN, Schlünzen F, Connell SR, Stachelhaus T, Zaborowska Z, Spahn CM. T, Fucini P. Mol. Cell 2008; 30: 26
• 7b Baumann S, Schoof S, Bolten M, Häring C, Takagi M, Shin-ya K, Arndt H.-D. J. Am. Chem. Soc. 2010; 132: 6973
• 8a Depaire H, Thomas JP, Brun A, Lukacs G. Tetrahedron Lett. 1977; 18: 1395
• 8b Depaire H, Thomas JP, Brun A, Olesker A, Lukacs G. Tetrahedron Lett. 1977; 18: 1403
• 9a Houck DR, Chen LC, Keller PJ, Beale JM, Floss HG. J. Am. Chem. Soc. 1987; 109: 1250
• 9b Houck DR, Chen LC, Keller PJ, Beale JM, Floss HG. J. Am. Chem. Soc. 1988; 110: 5800
• 9c Mocek U, Knaggs AR, Tsuchiya R, Nguyen T, Beale JM, Floss HG. J. Am. Chem. Soc. 1993; 115: 7557
• 10a Prange T, Ducruix S, Pascard C, Lunel J. Nature (London) 1977; 265: 189
• 10b Pascard C, Ducroix A, Lunel J, Prange T. J. Am. Chem. Soc. 1977; 99: 6418
• 11 Yu Y, Duan L, Zhang Q, Liao RJ, Ding Y, Pan H.-X, Wendt-Pienkowski E, Tang GL, Shen B, Liu W. ACS Chem. Biol. 2009; 4: 855
• 12 For a discussion see: Arndt H.-D, Schoof S, Lu J.-Y. Angew. Chem. Int. Ed. 2009; 48: 6770; and references cited therein
• 13 Benazet F, Cartier JR. Poult. Sci. 1980; 59: 1405
• 14a Jayasuriya H, Herath K, Ondeyka JG, Zhang C, Zink DL, Brower M, Gailliot FP, Greene J, Birdsall G, Venugopal J, Ushio M, Burgess B, Russotti G, Walker A, Hesse M, Seeley A, Junker B, Connors N, Salazar O, Genilloud O, Liu K, Masurekar P, Barrett JF, Singh SB. J. Antibiot. 2007; 60: 554
• 14b Zhang C, Herath K, Jayasuriya H, Ondeyka JG, Zink D.hL, Occi J, Birdsall G, Venugopal J, Ushio M, Burgess B, Masurekar P, Barrett JF, Singh SB. J. Nat. Prod. 2009; 72: 841

Thiopeptide total synthesis work after 2009:
• 15a Lefranc D, Ciufolini MA. Angew. Chem. Int. Ed. 2009; 48: 4198
• 15b Ammer C, Bach T. Chem. Eur. J. 2010; 16: 14083
• 15c Aulakh VS, Ciufolini MA. J. Am. Chem. Soc. 2011; 133: 5900

Synthesis of indole fragments:
• 16a Koerber-Plé K, Massiot G. Synlett 1994; 759
• 16b Shin C.-g, Yamada Y, Hayashi K, Yonezawa Y, Umemura K, Tanji T, Yoshimura J. Heterocycles 1996; 43: 891
• 16c Bentley DJ, Fairhurst J, Gallagher PT, Manteuffel AK, Moody CJ, Pinder JL. Org. Biomol. Chem. 2004; 2: 701

Synthesis of thiazole fragments:
• 16d Iwakama M, Kobayashi Y, Ikuta S, Yoshimura J. Chem. Lett. 1982; 1975
• 16e Koerber-Plé K, Massiot G. J. Heterocycl. Chem. 1995; 32: 1309
• 16f Shin C, Nakamura Y, Yamada Y, Yonezawa Y, Umemura K, Yoshimura J. Bull. Chem. Soc. Jpn. 1995; 68: 3151
• 16g Umemura K, Tate T, Yamaura M, Yoshimura J, Yonezawa Y, Shin C.-g. Synthesis 1995; 1423
• 16h Belhadj T, Nowicki A, Moody CJ. Synlett 2006; 3033

Synthesis of the 3-hydroxypyridine core:
• 16i Umemura K, Noda H, Yoshimura J, Konn A, Yonezawa Y, Shin C.-g. Tetrahedron Lett. 1997; 38: 3539
• 16j Yonezawa Y, Konn A, Shin C.-g. Heterocycles 2004; 63: 2735
• 16k Taddei D, Poriel C, Moody CJ. ARKIVOC 2007; 11: 56
• 17a Nicolaou KC, Lee SH, Estrada AA, Zak M. Angew. Chem. Int. Ed. 2005; 44: 3736
• 17b Nicolaou KC, Estrada AA, Freestone GC, Lee SH, Alvarez-Mico X. Tetrahedron 2005; 63: 6088
• 18 Kimber MC, Moody CJ. Chem. Commun. 2008; 591
• 19 Lu J.-Y, Riedrich M, Mikyna M, Arndt H.-D. Angew. Chem. Int. Ed. 2009; 48: 8137
• 20a Riedrich M, Harkal SD, Arndt H.-D. Angew. Chem. Int. Ed. 2007; 46: 2701
• 20b Loos P, Riedrich M, Arndt H.-D. Chem. Commun. 2009; 1900
• 21a Lu J.-Y, Arndt H.-D. J. Org. Chem. 2007; 72: 4205
• 21b Lu J.-Y, Shen W.-Z, Preut H, Arndt H.-D. Acta Crystallogr., Sect. E 2008; 64: o602
• 21c Lu J.-Y, Keith J, Shen W.-Z, Schürmann M, Preut H, Jacob T, Arndt H.-D. J. Am. Chem. Soc. 2008; 130: 13219
• 22 Herbert JM. Tetrahedron Lett. 2004; 45: 817
• 23 Lapatsanis L. Tetrahedron Lett. 1978; 19: 4697
• 24 Grieco PA, Gilman S, Nishizawa M. J. Org. Chem. 1976; 41: 1485
• 25a Miller MJ. J. Org. Chem. 1980; 45: 3131
• 25b Fukase K, Kitazawa M, Sano A, Shimbo K, Horimoto S, Fujita H, Kubo A, Wakamiya T, Shibe A. Bull. Chem. Soc. Jpn. 1992; 65: 2227
• 25c Bayó N, Jiménez JC, Rivas L, Nicolás E, Albericio F. Chem. Eur. J. 2003; 9: 1096
• 26 Dessolin M, Guillerez M.-G, Thieriet N, Guibe F, Loffet A. Tetrahedron Lett. 1995; 36: 5741
• 27 Bowers-Nemia MM, Joullié MM. Heterocycles 1983; 20: 817
• 28a Zhang X, Schmitt AC, Jiang W. Tetrahedron Lett. 2001; 42: 5335
• 28b Waldmann H, He Y.-P, Tan H, Arve L, Arndt H.-D. Chem. Commun. 2008; 5562
• 28c Review: Plietker B. Synthesis 2005; 2453
• 29 Sakaitani M, Ohfune Y. J. Org. Chem. 1990; 55: 870
• 30 Kruse PF, Geurkink N, Grist KL. J. Am. Chem. Soc. 1954; 76: 5796
• 31 Kuhn R, Dury K. Justus Liebigs Ann. Chem. 1951; 571: 44
• 32 Delgado O, Müller HM, Bach T. Chem. Eur. J. 2008; 14: 2322
• 33 Luo Y, Evindar G, Fishlock D, Lajoie GA. Tetrahedron Lett. 2001; 42: 3807
• 34 Nicolaou KC, Estrada AA, Zak M, Lee SH, Safina BS. Angew. Chem. Int. Ed. 2005; 44: 1378
• 35 Li H, Jiang X, Ye Y.-H, Fan C, Romoff T, Goodman M. Org. Lett. 1999; 1: 91
• 36 Lu J.-Y. Dissertation . TU-Dortmund; Germany: 2009
• 37 Dawson PE, Muir TW, Clark-Lewis I, Kent SB. H. Science (Washington, D. C.) 1994; 266: 773
• 38 Bang D, Kent SB. H. Angew. Chem. Int. Ed. 2004; 43: 2534
• 39 Riedrich M. Dissertation . TU-Dortmund; Germany: 2009
• 40 Isidro-Llobet A, Álvarez M, Albericio F. Chem. Rev. 2009; 109: 2455
• 41 Kaiser E, Picart F, Kubiak T, Tam JP, Merrifield RB. J. Org. Chem. 1993; 58: 5167
• 42a Coleman RS, Shah JA. Synthesis 1999; 1399
• 42b Felix AM, Heimer EP, Lambros TJ, Tzougraki C, Meienhofer J. J. Org. Chem. 1978; 43: 4194
• 42c Brastianos HC, Vottero E, Patrick BO, van Soest R, Matainaho T, Mauk AG, Andersen RJ. J. Am. Chem. Soc. 2006; 128: 16046
• 43 Anson MS, Montana JG. Synlett 1994; 219
• 44 Crich D, Vinogradova O. J. Org. Chem. 2007; 72: 3581
• 45a Li WR, Lin YS, Yo YC. Tetrahedron Lett. 2000; 41: 6619
• 45b Tsuji T, Kataoka T, Yoshioka M, Sendo Y, Nishitani Y, Hirai S, Maeda T, Nagata W. Tetrahedron Lett. 1979; 20: 2793
• 46 Kamal A, Laxman E, Rao NV. Tetrahedron Lett. 1999; 40: 371
• 47 Saady M, Lebeau L, Mioskowski C. J. Org. Chem. 1995; 60: 2946
• 48 Further experimental procedures and data can be found in the Supporting Information.
• 49 Zinc powder was suspended in 2% HCl, stirred for 1 min, drained, and washed with 2% HCl (3 ×), H₂O (3 ×), EtOH (3 ×) and Et₂O.