Synlett 2013; 24(15): 1915-1920
DOI: 10.1055/s-0033-1338974
letter
© Georg Thieme Verlag Stuttgart · New York

Toward the Total Synthesis of Divergolides C and D

Anastasia Hager
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany   Email: [email protected]
,
Christian A. Kuttruff
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany   Email: [email protected]
,
Dominik Hager
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany   Email: [email protected]
,
Daniel W. Terwilliger
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany   Email: [email protected]
,
Dirk Trauner*
Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany   Email: [email protected]
› Author Affiliations
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

 
  • References


    • For recent examples of divergent total synthesis, see:
    • 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
    • 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).