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Effective formal synthesis of benzomalvin A

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Abstract

A short and effective strategy for the construction of the tetracyclic core structure of the biologically active compound benzomalvin A from cheap commercially available (S)-phenylalanine and isatoic anhydride is described. This three-pot methodology was successfully implemented to synthesize N-demethylbenzomalvin A on a multi-gram scale with 54% overall yield.

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References

  1. Sun HH, Barrow CJ, Sedlock DM, Gillum AM, Cooper RJ (1994) Antibiot 47:515

    CAS  Google Scholar 

  2. Sun HH, Barrow CJ, Cooper RJ (1995) J Nat Prod 58:1575

    Article  CAS  Google Scholar 

  3. Sugimori T, Okawa T, Eguchi S, Yashima E, Okamoto Y (1997) Chem Lett 869

  4. Sugimori T, Okawa T, Eguchi S, Kakehi A, Yashima E, Okamoto Y (1998) Tetrahedron 58:7997

    Article  Google Scholar 

  5. Liu J, Kaselj M, Isome Y, Chapnick J, Zhang B, Bi G, Yahannes D, Yu L, Baldino J (2005) J Org Chem 70:10488

    Article  CAS  Google Scholar 

  6. Grieder A, Thomson AW (2003) Synthesis 1707

  7. Zhang W, Williams JP, Lu Y, Nagashima T, Chu Q (2007) Tetrahedron Lett 48:563

    Article  CAS  Google Scholar 

  8. Tseng MC, Yang HY, Chu YH (2010) Org Biomol Chem 8:419

    Article  CAS  Google Scholar 

  9. Zhichkin PE, Jin X, Zhang H, Peterson LH, Ramirez C, Snyder TM, Burton HS (2010) Org Biomol Chem. doi: 10.1039/b925494c

  10. Al-Said NH, Al-Qaisi LS (2006) Acta Chim Slov 53:204

    CAS  Google Scholar 

  11. Al-Said NH, Al-Qaisi LS (2006) Tetrahedron Lett 47:693

    Article  CAS  Google Scholar 

  12. Al-Said NH, Ishtaiwi Z (2005) Acta Chim Slov 52:328

    CAS  Google Scholar 

  13. Taher D, Ishtaiwi Z, Al-Said NH (2008) Arkivoc xvi:154

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Acknowledgments

This work was supported by the Deanship of Research at Jordan University of Science and Technology.

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Authors and Affiliations

  1. Department of Applied Chemical Sciences, Jordan University of Science and Technology, Irbid, 22110, Jordan

    Naim H. Al-Said

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  1. Naim H. Al-Said
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Correspondence to Naim H. Al-Said.

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Al-Said, N.H. Effective formal synthesis of benzomalvin A. Monatsh Chem 141, 1249–1251 (2010). https://doi.org/10.1007/s00706-010-0387-0

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  • DOI: https://doi.org/10.1007/s00706-010-0387-0

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