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Synthesis 2014; 46(21): 2927-2936
DOI: 10.1055/s-0034-1379003
DOI: 10.1055/s-0034-1379003
paper
Exploring a Ring-Closing Metathesis Approach to the Archazolid Macrocycle
Further Information
Publication History
Received: 17 June 2014
Accepted after revision: 28 July 2014
Publication Date:
15 August 2014 (online)
Abstract
The synthesis of a new ‘eastern domain’ of a proposed dihydroarchazolid analogue is described along with initial results from attempted macrocyclization by ring-closing metathesis. This work has revealed a competing backbiting process that may be preventable by alcohol functionalization and installation of a metathesis relay.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084. Included are spectral data for compounds 9, 10, 12, 13, 17, 18–26.
- Supporting Information
-
References
- 1a Höfle G, Reichenbach H, Sasse F, Steinmetz H. German Patent DE 41 32 951 C1, 1993
- 1b Höfle G, Reichenbach H, Sasse F, Steinmetz H. J. Antiobiot. Chem. 2003; 56: 520
- 2 Huss M, Wieczorek H. J. Exp. Biol. 2009; 212: 341
- 3 Wiedmann RM, von Schwarzenberg K, Palamidessi A, Schreiner L, Kubisch R, Liebl J, Schempp C, Trauner D, Vereb G, Zahler S, Wagner E, Müller R, Scita G, Vollmar AM. Cancer Res. 2012; 72: 5976
- 4 Kubisch R, Fröhlich T, Arnold GJ, Schreiner L, von Schwarzenberg K, Roidl A, Vollmar AM, Wagner E. Int. J. Cancer 2014; 134: 2478
- 5 For examples of dihydro-natural product analogues, see: Zhu W, Jiménez M, Jung W-H, Camarco DP, Balachandran R, Vogt A, Day BW, Curran DP. J. Am. Chem. Soc. 2010; 132: 9175
- 6 For an example of reported 1,4-diene sensitivity in the context of natural product synthesis, see: Vilotijevic I, Jamison TF. Science 2007; 317: 1189
- 7 Tran AB, Melly G, Doucette R, Ashcraft B, Sebren L, Young J, O’Neil GW. Org. Biomol. Chem. 2011; 9: 7671
- 8 O’Neil GW, Black MJ. Synlett 2010; 107
- 9 White JD, Carter P, Kezar HS. J. Org. Chem. 1982; 47: 929
- 10 Van Horn DE, Negishi E-i. J. Am. Chem. Soc. 1978; 100: 2252
- 11 Molander GA, Fumagalli T. J. Org. Chem. 2006; 71: 5743
- 12 Hassfeld J, Kalesse M. Synlett 2002; 2007
- 13 Wipf P, Lim S. Angew. Chem., Int. Ed. Engl. 1993; 32: 1068
- 14a Cram DJ, Kopecky KR. J. Am. Chem. Soc. 1959; 81: 2748
- 14b Reetz MT. Acc. Chem. Res. 1993; 26: 462
- 14c The stereochemistry was determined by detailed NMR analysis after conversion to the corresponding PMP acetal (Figure 2):
- 15 Still WC, Gennari C. Tetrahedron Lett. 1983; 24: 4405
- 16 Hensel MJ, Fuchs PL. Synth. Commun. 1986; 16: 1285
- 17 Huang X, Pi J-P. Tetrahedron Lett. 2004; 45: 2215
- 18 Hudrlik PF, Peterson D. J. Am. Chem. Soc. 1975; 97: 1464
- 19 Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M. Bull. Chem. Soc. Jpn. 1979; 52: 1989
- 20a Menche D, Hassfeld J, Li J, Rudolph S. J. Am. Chem. Soc. 2007; 129: 6100
- 20b Menche D, Hassfeld J, Li J, Mayer K, Rudolph S. J. Org. Chem. 2009; 74: 7220
- 21 Jung W-H. Doctoral Dissertation . University of Pittsburg; USA: 2008
- 22 Roethle PA, Ingrid TC, Trauner D. J. Am. Chem. Soc. 2007; 129: 8960
- 23a Trnka TM, Grubbs RH. Acc. Chem. Res. 2001; 34: 18
- 23b Garber SB, Kingsbury JS, Gray BL, Hoveyda AH. J. Am. Chem. Soc. 2000; 122: 8168
- 24 BouzBouz S, Simmons R, Cossy J. Org. Lett. 2004; 6: 3465
- 25 For an example of a similar backbiting, see: Zhu W, Jiménez M, Jung W-H, Camarco DP, Balachandran R, Vogt A, Day BW, Curran DP. J. Am. Chem. Soc. 2010; 132: 9175
- 26 Hoye TR, Jeffrey CS, Tennakoon MA, Wang J, Zhao H. J. Am. Chem. Soc. 2004; 126: 10210
- 27a O’Neil GW, Moser DJ, Volz EO. Tetrahedron Lett. 2009; 50: 7355
- 27b Carter KP, Moser DJ, Storvick JM, O’Neil GW. Tetrahedron Lett. 2011; 52: 4494
- 27c Storvick JK, Ankoudinova E, King BR, Van Epps H, O’Neil GW. Tetrahedron Lett. 2011; 52: 5858
- 28 Crimmins MT, Chaudhary K. Org. Lett. 2000; 2: 775
- 29 Fürstner A, Fasching B, O’Neil GW, Fenster MD. B, Godbout C, Ceccon J. Chem. Commun. 2007; 3045