Synthesis 2014; 46(02): 189-194
DOI: 10.1055/s-0033-1338558
paper
© Georg Thieme Verlag Stuttgart · New York

First Total Synthesis of (–)-Auranomide C and Its Derivatives

Kumaraswamy Sorra*
a   Chemistry Services, GVK Biosciences Private Limited, Plot No.28A, IDA Nacharam, Hyderabad 500076, AP, India   Fax: +91(40)66281505   eMail: kumaraswamy.s@gvkbio.com
b   Chemistry Division, Institute of Science and Technology, JNT University, Kukatpally, Hyderabad 500072, AP, India
,
K. Mukkanti
b   Chemistry Division, Institute of Science and Technology, JNT University, Kukatpally, Hyderabad 500072, AP, India
,
Srinivas Pusuluri
a   Chemistry Services, GVK Biosciences Private Limited, Plot No.28A, IDA Nacharam, Hyderabad 500076, AP, India   Fax: +91(40)66281505   eMail: kumaraswamy.s@gvkbio.com
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 15. August 2013

Accepted after revision: 24. Oktober 2013

Publikationsdatum:
14. November 2013 (online)


Abstract

The first total synthesis of (–)-auranomide C has been achieved. The short synthetic strategy involves a reductive dehydrocyclization and the nucleophilic ring opening of a fused γ-lactam. The route allows for ease in synthesizing diverse derivatives in the side chain of the natural product.

Supporting Information

 
  • References

  • 1 Song F, Ren B, Yu K, Chen C, Guo H, Yang N, Gao H, Liu X, Liu M, Tong Y, Dai H, Bai H, Wang J, Zhang L. Mar. Drugs 2012; 10: 1297
    • 2a Goetz MA, Lopez M, Monaghan RL, Chang RS. L, Lotti VJ, Chen TB. J. Antibiot. 1985; 38: 1633
    • 2b Chang RS. L, Lotti VJ, Monaghan RL, Birnbaum J, Stapley EO, Goetz MA, Albers-Schonberg G, Patchett AA, Liesch JM, Hensens OD, Springer JP. Science (Washington, D.C.) 1985; 230: 177
    • 2c Goetz MA, Monaghan RL, Chang RS. L, Ondeyka J, Chen TB, Lotti VJ. J. Antibiot. 1988; 41: 875
    • 2d Sun HH, Barrow CJ, Sedlock DM, Gillum AM, Cooper R. J. Antibiot. 1994; 47: 515
    • 3a Joshi BK, Gloer JB, Wicklow DT, Dowd PF. J. Nat. Prod. 1999; 62: 650
    • 3b Dai J.-R, Carte BK, Sidebottom PJ, Yew AL. S, Ng SW, Huang Y, Butler MS. J. Nat. Prod. 2001; 64: 125
    • 3c Raebaek L, Breinholt J. J. Nat. Prod. 1999; 62: 904
    • 3d Raebaek L, Breinholt J, Frisvald JC, Christopherson C. J. Org. Chem. 1999; 64: 1689
    • 3e Ookura R, Kito K, Ooi T, Namikoshi M, Kusumi T. J. Org. Chem. 2008; 73: 4245
    • 4a Bock MG, DiPardo RM, Rittle KE, Evans BE, Freidinger RM, Veber DF, Chang RS. L, Chen TB, Keegan ME, Lotti VJ. J. Med. Chem. 1986; 29: 1941
    • 4b Lopez-Gresa MP, Gonzalez MC, Primo J, Moya P, Romero V, Estornell E. J. Antibiot. 2005; 58: 416
    • 5a Snider BB, Busuyek MV. Tetrahedron 2001; 57: 3301
    • 5b He F, Foxman BM, Snider BB. J. Am. Chem. Soc. 1998; 120: 6417
    • 5c Grieder A, Thomas AW. Synthesis 2003; 1707
    • 5d Sugimori T, Okawa T, Eguchi S, Kakehi A, Yashima E, Okamoto Y. Tetrahedron 1998; 54: 7997
    • 5e Eguchi S. ARKIVOC 2005; (ii): 98
    • 5f Bose DS, Chary MV. Synthesis 2010; 643
  • 6 Witt A, Bergman J. J. Org. Chem. 2001; 66: 2784
  • 7 Bock MG, DiPardo RM, Pitzenberger SM, Homnick CF, Springer JP, Freidinger RM. J. Org. Chem. 1987; 52: 1646
  • 8 Liu JF, Kaselj M, Isome Y, Chapnick J, Zhang B, Bi G, Yohannes D, Yu L, Baldino CM. J. Org. Chem. 2005; 70: 10488
    • 9a Zhichkin PE, Jin X, Zhang H, Peterson LH, Ramirez C, Snyder TM, Burton HS. Org. Biomol. Chem. 2010; 8: 1287
    • 9b Tseng MC, Yang HY, Chu YH. Org. Biomol. Chem. 2010; 8: 419
  • 10 Kshirsagar UA, Argade NP. Org. Lett. 2010; 12: 3716
  • 11 Kumaraswamy S, Mukkanti K, Srinivas P. Tetrahedron 2012; 68: 2001
  • 12 Cheng M.-F, Yu H.-M, Ko B.-W, Chang Y, Chen M.-Y, Ho T.-I, Tsai Y.-M, Fang J.-M. Org. Biomol. Chem. 2006; 4: 510
  • 13 Witt A, Gustavsson A, Bergman J. J. Heterocycl. Chem. 2003; 40: 29
  • 14 The enantiomeric purity was determined by comparing chiral HPLC area method with a racemic compound 3 which was synthesized similarly from the dimethyl dl-glutamate.