BF3·OEt2-catalyzed synthesis of 1-(tetrahydropyran-3-yl)-1,3-dihydroisobenzofuran and trans-fused hexahydropyrano[3,2-c]chromene derivatives

Tetrahedron Letters

Volumn 55, Issue 30, 2014, Pages 4236-4239

  Syama Sundar, Ch ^a   Ramana Reddy, M ^b   Sridhar, B ^b   Kiran Kumar, S ^b   Suresh Reddy, C ^a   Reddy, B V Subba ^b  

^a SRI VENKATESWARA UNIVERSITY   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldehydes; CO, CC bond formation; Prins cascade cyclization

Indexed keywords

1 (TETRAHYDROPYRAN 3 YL) 1, 3 DIHYDROISOBENZOFURAN; ALDEHYDE; CHROMENE DERIVATIVE; ISOBENZOFURAN DERIVATIVE; SALICYLALDEHYDE; TETRAHYDROPYRAN DERIVATIVE; TRANS FUSED HEXAHYDROPYRANO[3,2 C]CHROMENE DERIVATIVE; UNCLASSIFIED DRUG; 1 (TETRAHYDROPYRAN 3 YL) 1, 3 DIHYDROISOBENZOFURAN DERIVATIVE; ALDEHYDE DERIVATIVE; BENZOFURAN DERIVATIVE;

ARTICLE; CATALYST; CYCLIZATION; ELECTRON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY; ANALYTIC METHOD; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 84904053664     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.05.083     Document Type: Article

References (33)

1. S.V. Jovanovic, S. Steenken, C.W. Boone, and M.G. Simic J. Am. Chem. Soc. 121 1999 9677
2. M.B. Gewali, Y. Tezuka, A.H. Banskota, M.S. Ali, I. Saiki, H. Dong, and S. Kadota Org. Lett. 1 1999 1733
3. H. Masuda, A. Ishikado, N. Nishida, K. Ninomiya, H. Fujiwara, Y. Kobayashi, and M. Yoshikawa Bioorg. Med. Chem. Lett. 8 1998 2939
4. Y. Tezuka, M.B. Gewali, M.S. Ali, A.H. Banskota, and S. Kadota J. Nat. Prod. 64 2001 208
5. S. Mitsui, S. Kobayashi, H. Nagahori, and A. Ogiso Chem. Pharm. Bull. 24 1976 2377
6. M.M. Chan, H.I. Huang, M.R. Fenton, and D. Fong Biochem. Pharmacol. 55 1998 1955
7. For recent reviews on the Prins reaction, see: C. Olier, M. Kaafarani, S.S. Gastaldi, and M.P. Bertrand Tetrahedron 66 2010 413
8. I.M. Pastor, and M. Yus Curr. Org. Chem. 11 2007 925
9. E.A. Crane, and K.A. Scheidt Angew. Chem., Int Ed. 122 2010 8494
10. J.S. Yadav, B.V.S. Reddy, T. Maity, and G.G.K.S.N. Kumar Tetrahedron Lett. 48 2007 7155
11. S.D. Rychnovsky, and C.R. Thomas Org. Lett. 2 2000 1217
12. P.O. Miranda, M.A. Ramirez, V.S. Martin, and J.I. Padron Org. Lett. 8 2006 1633
13. M.L. Bolla, B. Patterson, and S.D. Rychnovsky J. Am. Chem. Soc. 127 2005 16044
14. C.S. Barry, N. Bushby, J.P.H. Charmant, J.D. Elsworth, J.R. Harding, and C.L. Willis Chem. Commun. 40 2005 5097
15. P. Borkar, P.V.D. Weghe, B.V.S. Reddy, J.S. Yadav, and R. Gree Chem. Commun. 48 2012 9016
16. M.R. Gesinski, K. Tadpetch, and S.D. Rychnovsky Org. Lett. 11 2009 5342
17. M.S. Kwon, S.K. Woo, S.W. Na, and E. Lee Angew. Chem., Int. Ed. 47 2008 1733
18. S. Manaviazar, and K.J. Hale Angew. Chem., Int. Ed. 50 2011 8786
19. P.A. Wender, and A.J. Schrier J. Am. Chem. Soc. 133 2011 9228
20. S.K. Woo, M.S. Kwon, and E. Lee Angew. Chem., Int. Ed. 47 2008 3242
21. M.R. Gesinski, and S.D. Rychnovsky J. Am. Chem. Soc. 133 2011 9727
22. H.Y. Lin, and B.B. Snider Org. Lett. 13 2011 1234
23. K.B. Bahnck, and S.D. Rychnovsky J. Am. Chem. Soc. 130 2008 13177
24. F.K. Chio, J. Warne, D. Gough, M. Penny, S. Green, S.J. Coles, M.B. Hursthouse, P. Jones, L. Hassall, T.M. McGuire, and A.P. Dobbs Tetrahedron 67 2011 5107
25. B.V.S. Reddy, P. Borkar, P.P. Chakravarthy, J.S. Yadav, and R. Grée Tetrahedron Lett. 51 2010 3412
26. B.V.S. Reddy, P. Borkar, J.S. Yadav, B. Sridhar, and R. Grée J. Org. Chem. 76 2011 7677
27. B.V.S. Reddy, P. Borkar, J.S. Yadav, P.P. Reddy, A.C. Kunwar, B. Sridhar, and R. Gree Org. Biomol. Chem. 10 2012 1349
28. J.S. Yadav, P. Borkar, P.P. Chakravarthy, B.V.S. Reddy, A.V.S. Sarma, B. Sridhar, and R. Grée J. Org. Chem. 75 2010 2081
29. H.M. Ko, D.G. Lee, M.A. Kim, H.J. Kim, J. Park, M.S. Lah, and E. Lee Tetrahedron 63 2007 5797
30. J.S. Yadav, N. Thrimurtulu, K.U. Gayathri, B.V.S. Reddy, and A.R. Prasad Tetrahedron Lett. 49 2008 6617
31. J.S. Yadav, K.L. Lakshmi, N.M. Reddy, A.R. Prasad, and B.V.S. Reddy Tetrahedron 44 2010 334
32. J.S. Yadav, B. Padmavani, B.V.S. Reddy, Ch. Venugopal, and A.B. Rao Synlett 2007 2045
33. CCDC-992340 contains supplementary crystallographic data for compound 2a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif. Organisation