First total synthesis and structure confirmation of diacetylenic polyol (+)-oploxyne B

Tetrahedron Letters

Volumn 54, Issue 41, 2013, Pages 5616-5618

  Srihari, P ^a   Sathish Reddy, A ^a   Yadav, J S ^a   Yedlapudi, D ^a   Kalivendi, Shasi V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Acetonide; Bromo acetylene; Cadiot Chodkiewicz coupling; Ohira Bestmann; Polyacetylene

Indexed keywords

NATURAL PRODUCT; OPLOXYNE B; POLYOL; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; STEREOCHEMISTRY;

EID: 84883490277     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.08.020     Document Type: Article

References (27)

1. B.W. Gung C. R. Chim. 12 2009 489 505
2. For review see L.K. Annabelle, S. Shun, and R.R. Tykwinski Angew. Chem., Int. Ed. 45 2006 1034 1057 and references cited there in
3. R.E. Minto, and B.J. Blacklock Prog. Lipid Res. 47 2008 233 306
4. M.L. Lerch, M.K. Harper, and D.J. Faulkner J. Nat. Prod. 66 2003 667 670
5. G.-X. Zhou, and T.F. Molinski Mar. Drugs 1 2003 46 53
6. A.E. Wright, O.J. McConnell, S. Kohmoto, M.S. Lui, W. Thompson, and K.M. Snader Tetrahedron Lett. 28 1987 1377 1379
7. M.C. Yang, H.C. Kwon, Y.-J. Kim, K.R. Lee, and H.O. Yang J. Nat. Prod. 73 2010 801 805
8. J.S. Yadav, B. Kumaraswamy, A. Sathish Reddy, P. Srihari, R.V. Janakiram, and S.V. Kalivendi J. Org. Chem. 76 2011 2568 2576
9. Y. Sridhar, and P. Srihari Eur. J. Org. Chem. 2013 578 587
10. Y. Sridhar, and P. Srihari Eur. J. Org. Chem. 2011 6690 6697
11. P. Srihari, B. Mahankali, and K. Rajendraprasad Tetrahedron Lett. 53 2012 56 58
12. P. Srihari, K. Satyanarayana, B. Ganganna, and J.S. Yadav J. Org. Chem. 76 2011 1922 1925
13. G. Sabitha, Ch.S. Reddy, P. Srihari, and J.S. Yadav Synthesis 2003 2699 2704
14. K.P. Jang, S.Y. Choi, Y.K. Chung, and E. Lee Org. Lett. 13 2011 2476 2479
15. D.K. Mohapatra, E.B. Reddy, P.S.K. Rao, P.P. Das, and J.S. Yadav Org. Lett. 13 2011 744 747
16. S. Ohira Synth. Commun. 19 1989 561 564
17. S. Muller, B. Liepold, G.J. Roth, and H.J. Bestmann Synlett 1996 521 522
18. P.W. Feit J. Med. Chem. 7 1964 14 17
19. F. Toda, and K. Tanaka Tetrahedron. Lett. 29 1988 551 554
20. E. Roulland Angew. Chem., Int. Ed. 47 2008 3762 3765
21. S. Takahashi, N. Ogawa, H. Koshino, and T. Nakata Org. Lett. 7 2005 2783 2786
22. M. Frigerio, M. Santagostino, and S. Sputore J. Org. Chem. 64 1999 4537 4538
23. J. Garegg, and B. Samuelsson J. Chem. Soc. Perkin I 1980 2866 2869
24. The allyl alcohol can also be prepared from iodide through Boord reaction conditions wherein Zinc is used to get the reductive elimination C. Schneider, and U. Kazmaier Synthesis 1998 1314 1320
25. The procedure for bromination was followed from H. Yun, and S.J. Danishefsky J. Org. Chem. 68 2003 4519 4522
26. P. Cadiot, and W. Chodkiewicz H.G. Viehe, Chemistry of Acetylenes 1969 Marcel Dekker New York 597 647
27. T. Mosmann J. Immunol. Methods 65 1983 55 63