Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2013; 24(15): 1915-1920
DOI: 10.1055/s-0033-1338974
DOI: 10.1055/s-0033-1338974
letter
Toward the Total Synthesis of Divergolides C and D
Further Information
Publication History
Received: 16 June 2013
Accepted: 25 June 2013
Publication Date:
21 August 2013 (online)
Abstract
The divergolides are a family of structurally unprecedented ansa macrocycles. We describe a synthetic strategy toward divergolides C and D that hinges on the biomimetic diversification of a common intermediate. An advanced precursor that incorporates all the carbon atoms of divergolide C and D is presented, and atropisomerism in a sterically crowded acyl naphthalene is studied.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett. Included are experimental details, spectroscopic and analytical data for all new compounds (including X-ray data for 20, 21 and 22, as well as for 26 and 27).
- Supporting Information
-
References
- 1a Chen K, Baran PS. Nature 2009; 459: 824
- 1b Jones SB, Simmons B, Mastracchio A, MacMillan DW. C. Nature 2011; 475: 183
- 1c Chiyoda K, Shimokawa J, Fukuyama T. Angew. Chem. Int. Ed. 2012; 51: 2505
- 2 Ding L, Maier A, Fiebig H.-H, Görls H, Lin W.-H, Peschel G, Hertweck C. Angew. Chem. Int. Ed. 2011; 50: 1630
- 3a Zhao G, Wu J, Dai W.-M. Synlett 2012; 23: 2845
- 3b Rasapalli S, Jarugumilli G, Yarrapothu GR, Golen JA, Rheingold AL. Org. Lett. 2013; 15: 1736
- 3c Rasapalli S, Jarugumilli G, Yarrapothu GR, Golen JA, Rheingold AL. Tetrahedron Lett. 2013; 54: 2615
- 4 Kuttruff CA. PhD Thesis. LMU München; Germany: 2012
- 5 Xu Z, Ding L, Hertweck C. Angew. Chem. Int. Ed. 2011; 50: 4667
- 6a Cai P, Kong FM, Ruppen ME, Glasier G, Carter GT. J. Nat. Prod. 2005; 68: 1736
- 6b Pennington LI, Moody CJ. Abstracts of Papers of the ACS 238th National Meeting, August 16th, 2009 . American Chemical Society; Washington, DC: 2009. Abstract number ORGN 387
- 7a Brown HC, Bhat KS. J. Am. Chem. Soc. 1986; 108: 5919
- 7b Brown HC, Jadhav PK, Bhat KS. J. Am. Chem. Soc. 1988; 110: 1535
- 7c Roush WR In Comprehensive Organic Synthesis . Trost BM. Fleming I.; Pergamon Press; Oxford: 1991: 1
- 8 Yin N, Wang G, Qian M, Negishi E. Angew. Chem. Int. Ed. 2006; 45: 2916
- 9 Phillips DJ, Pillinger KS, Li W, Taylor AE, Graham AE. Chem. Commun. 2006; 2280
- 10a Tomioka K, Suenaga T, Koga K. Tetrahedron Lett. 1986; 27: 369
- 10b Dambacher J, Anness R, Pollock P, Bergdahl M. Tetrahedron 2004; 60: 2097
- 10c Adam W, Zhang A. Eur. J. Org. Chem. 2004; 147
- 11 X-ray structures in cif format for compounds 20, 21, and 22 are available at the Cambridge Crystallographic Data Center (registration numbers CCDC 894000, 894001, and 894001, respectively).
- 12a Barrett AG. M, Carr RA. E, Attwood SV, Richardson G, Walshe ND. A. J. Org. Chem. 1986; 51: 4840
- 12b Gupta RC, Larsen DS, Stoodley RJ, Slawin AM. Z, Williams DJ. J. Chem. Soc., Perkin Trans. 1 1989; 739
- 12c Clive DL. J, Bergstra RJ. J. Org. Chem. 1991; 56: 4976
- 12d Miyashita M, Yamasaki T, Shiratani T, Hatakeyama S, Miyazawa M, Irie H. Chem. Commun. 1997; 18: 1787
-
12e Yamashita Y, Saito S, Ishitani H, Kobayashi S. J. Am. Chem. Soc. 2003; 125: 3793
- 13 Nawrat CC, Lewis W, Moody CJ. J. Org. Chem. 2011; 76: 7872
- 14 Kuttruff CA, Geiger S, Cakmak M, Mayer P, Trauner D. Org. Lett. 2012; 14: 1070
- 15 X-ray structures in cif format for compounds 26 and 27 are available at the Cambridge Crystallographic Data Center (registration numbers CCDC933387 and 933388, respectively).
For recent examples of divergent total synthesis, see:
For a similar situation encountered in the isolation of hygrocins, see: