Synthesis 2015; 47(05): 653-658
DOI: 10.1055/s-0034-1379709
paper
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Total Synthesis of Pinolide and Its C2 Epimer and Evaluation of Their Cytotoxic Activity[1]

Paramesh Jangili
a  Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India   Email: biswanathdas@yahoo.com
,
C. Ganesh Kumar
b  Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
,
Y. Poornachandra
b  Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
,
Biswanath Das*
a  Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India   Email: biswanathdas@yahoo.com
› Author Affiliations
Further Information

Publication History

Received: 19 September 2014

Accepted after revision: 19 November 2014

Publication Date:
11 December 2014 (eFirst)

Abstract

Pinolide, a naturally occurring nonenolide and its C2 epimer have been synthesized using d-mannitol and 1,2-epoxyhex-5-ene as the starting materials. The synthesis involves the Jacobsen’s hydrolytic kinetic resolution, Yamaguchi esterification, and intramolecular ring-closing metathesis as the key steps. The 2-epi-pinolide, the C2 epimer of pinolide, has been synthesized for the first time. The cytotoxic activity of the pinolide and 2-epi-pinolide has been studied.

 
  • References and notes

  • 1 Part 79 in the series Synthetic studies on natural products.
  • 2 Sun P, Lu S, Ree TV, Krohn K, Li L, Zhang W. Curr. Med. Chem. 2012; 9: 3417
    • 3a Rivero-Cruz JF, Garcia-Aguirre G, Cerda-Garcia-Rojas CM, Mata R. Tetrahedron 2000; 56: 5337
    • 3b Boonphong S, Kittakoop P, Isaka M, Pittayakhajonwut D, Tanticharoen M, Thebtaranonth Y. J. Nat. Prod. 2001; 64: 965
    • 3c Tsuda M, Mugishima T, Komatsu K, Sone T, Tanaka M, Mikami Y, Kobayashi J. J. Nat. Prod. 2003; 66: 412
    • 3d Riatto VB, Pilli RA, Victor MM. Tetrahedron 2008; 64: 2279
  • 4 Cimmino A, Andolfi A, Fondevilla S, Abouzeid MA, Rubiales D, Evidente A. J. Agric. Food Chem. 2012; 60: 5273
  • 5 Yadav JS, Avuluri S, Kattela SS, Das S. Eur. J. Org. Chem. 2013; 6967
    • 6a Reddy PR, Lingaiah M, Das B. Synlett 2014; 25: 975
    • 6b Maram L, Das B. Synthesis 2014; 46: 1205
    • 6c Reddy CR, Das B. Tetrahedron Lett. 2014; 55: 67
  • 7 Yadav VK, Agarwal D. Chem. Commun. 2007; 5232
  • 8 Jangili P, Kashanna J, Kumar GC, Poornachandra Y, Das B. Bioorg. Med. Chem. Lett. 2014; 24: 325
  • 9 Schaus SE, Brandes BD, Larrow JF, Tokunaga M, Hansen KB, Gould AE, Furrow ME, Jacobsen EN. J. Am. Chem. Soc. 2002; 124: 1307
  • 10 Epp JB, Widlanski TS. J. Org. Chem. 1999; 64: 293
  • 11 Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M. Bull. Chem. Soc. Jpn. 1979; 52: 1989
  • 12 Scholl M, Ding S, Lee CW, Grubbs RH. Org. Lett. 1999; 1: 953
  • 13 Mosmann T. J. Immunol. Methods 1983; 65: 55