Synlett 2014; 25(11): 1487-1493
DOI: 10.1055/s-0033-1341082
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© Georg Thieme Verlag Stuttgart · New York

Synthetic Strategies toward the Indoxamycin Family

Chi He
Department of Chemistry, Zhejiang University, 148 Tianmushan Road, Hangzhou 310028, P. R. of China   Fax: +86(571)88273332   Email: hfding@zju.edu.cn
,
Chenlong Zhu
Department of Chemistry, Zhejiang University, 148 Tianmushan Road, Hangzhou 310028, P. R. of China   Fax: +86(571)88273332   Email: hfding@zju.edu.cn
,
Hanfeng Ding*
Department of Chemistry, Zhejiang University, 148 Tianmushan Road, Hangzhou 310028, P. R. of China   Fax: +86(571)88273332   Email: hfding@zju.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 14 January 2014

Accepted after revision: 10 March 2014

Publication Date:
03 April 2014 (online)

Abstract

Indoxamycins A–F represent a novel class of polyketides isolated from saline cultures of actinomycetes. Owing to their stereochemically congested tricyclic structure and potent biological activities, indoxamycins are attractive targets for synthetic chemists. This report discusses recent progress toward the total synthesis of indoxamycins both by Carreira’s group and ours.

 
  • References

  • 1 Fenical W, Jensen PR. Nat. Chem. Biol. 2006; 2: 666
  • 2 Sato S, Iwata F, Mukai T, Yamada S, Takeo J, Abe A, Kawahara H. J. Org. Chem. 2009; 74: 5502
  • 3 Jeker OF, Carreira EM. Angew. Chem. Int. Ed. 2012; 51: 3474
  • 4 He C, Zhu C, Dai Z, Tseng C.-C, Ding H. Angew. Chem. Int. Ed. 2013; 52: 13256
    • 5a Kasatkin A, Nakagawa T, Okamoto S, Sato F. J. Am. Chem. Soc. 1995; 117: 3881
    • 5b Yatsumonji Y, Nishimura T, Tsubouchi A, Noguchi K, Takeda T. Chem. Eur. J. 2009; 15: 2680
    • 6a Ito Y, Aoyama H, Hirao T, Mochizuki A, Saegusa T. J. Am. Chem. Soc. 1979; 101: 494
    • 6b Kende AS, Roth B, Sanfilippo PJ. J. Am. Chem. Soc. 1982; 104: 1784
    • 6c Kende AS, Roth B, Sanfilippo PJ, Blacklock TJ. J. Am. Chem. Soc. 1982; 104: 5808
    • 6d Toyota M, Wada T, Fukumoto K, Ihara M. J. Am. Chem. Soc. 1998; 120: 4916
  • 7 Sherry BD, Toste FD. J. Am. Chem. Soc. 2004; 126: 15978
  • 8 Zhang Z, Liu C, Kinder RE, Han X, Qian H, Widenhoefer RA. J. Am. Chem. Soc. 2006; 128: 9066
  • 9 Jeker OF. PhD Dissertation. ETH Zurich; Switzerland: 2013

    • For reviews on tandem reactions, see:
    • 10a Bunce RA. Tetrahedron 1995; 51: 13103
    • 10b Nicolaou KC, Montagnon T, Snyder SA. Chem. Commun. 2003; 551
    • 10c Padwa A. Pure Appl. Chem. 2004; 76: 1933
    • 11a Yamada H, Aoyagi S, Kibayashi C. Tetrahedron Lett. 1997; 38: 3027
    • 11b Oh CH, Rhim CY, Kim M, Park DI, Gupta AK. Synlett 2005; 2694
    • 11c Oh CH, Jung HH. Tetrahedron Lett. 1999; 40: 1535
    • 11d Oh CH, Jung HH, Kim JS, Cho SW. Angew. Chem. Int. Ed. 2000; 39: 752
  • 12 Trost BM, Rise F. J. Am. Chem. Soc. 1987; 109: 3161
  • 13 Wang L, Li P, Menche D. Angew. Chem. Int. Ed. 2010; 49: 9270

    • For selected applications in total synthesis, see:
    • 14a Engstrom KM, Mendoza MR, Navarro-Villalobos M, Gin DY. Angew. Chem. Int. Ed. 2001; 40: 1128
    • 14b Taber DF, Teng D. J. Org. Chem. 2002; 67: 1607
    • 14c Pelc MJ, Zakarian A. Org. Lett. 2005; 7: 1629
    • 14d Lu C.-D, Zakarian A. Angew. Chem. Int. Ed. 2008; 47: 6829
    • 14e Ilardi EA, Isaacman MJ, Qin Y.-c, Shelly SA, Zakarian A. Tetrahedron 2009; 65: 3261
    • 15a Bickart P, Carson FW, Jacobus J, Miller EG, Mislow K. J. Am. Chem. Soc. 1968; 90: 4869
    • 15b Tang R, Mislow K. J. Am. Chem. Soc. 1970; 92: 2100
    • 15c Evans DA, Andrews GC, Sims CL. J. Am. Chem. Soc. 1971; 93: 4956
    • 15d Evans DA, Andrews GC. Acc. Chem. Res. 1974; 7: 147

      For selected enantioselective Alder–ene reactions, see:
    • 16a Trost BM, Czeskis BA. Tetrahedron Lett. 1994; 35: 211
    • 16b Goeke A, Sawamura M, Kuwano R, Ito Y. Angew. Chem. Int. Ed. 1996; 35: 662
    • 16c Hatano M, Terada M, Mikami K. Angew. Chem. Int. Ed. 2001; 40: 249
    • 16d Hatano M, Mikami K. Org. Biomol. Chem. 2003; 1: 3871
    • 16e Hatano M, Mikami K. J. Am. Chem. Soc. 2003; 125: 4704
    • 16f Mikami K, Hatano M. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5767