Convergent synthesis of 2H-chromenes - A formal [3+3] cycloaddition by a one-pot, three-step cascade

Tetrahedron

Volumn 67, Issue 51, 2011, Pages 9779-9786

  Parker, Kathlyn A ^a,b   Mindt, Thomas L ^b,c  

^a STONY BROOK UNIVERSITY   (United States)

^b BROWN UNIVERSITY   (United States)

^c UNIVERSITY HOSPITAL BASEL   (Switzerland)

Author keywords

Cascade; Electrocyclization; Formal 3+3 cycloaddition; ortho Quinone methide; Stille coupling

Indexed keywords

BROMINE; CHROMENE DERIVATIVE; PALLADIUM; QUINONE DERIVATIVE; TIN DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STILLE REACTION;

EID: 81255185267     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.068     Document Type: Article

References (45)

1. See K.A. Parker, T.L. Mindt, and Y.-H. Koh Org. Lett. 8 2006 1759 1762 and references therein
2. Stannane 2 was used as a mixture of cis/trans isomers: P.W. Collins, S.W. Kramer, A.F. Gasiecki, R.M. Weier, P.H. Jones, G.W. Gullikson, and R.G. Bianchi J. Med. Chem. 30 1987 193 197
3. K.A. Parker, and T.L. Mindt Org. Lett. 3 2001 3875 3878
4. K. Bera, S. Sarkar, S. Biswas, S. Maiti, and U. Jana J. Org. Chem. 76 2011 3539 3544
5. L.-W. Ye, X.-L. Sun, C.-Y. Zhu, and Y. Tang Org. Lett. 8 2006 3853 3856
6. G. Lu, and H.C. Malinakova J. Org. Chem. 69 2004 4701 4715
7. A.V. Kurdyumov, R.P. Hsung, K. Ihlen, and J. Wang Org. Lett. 5 2003 3935 3938
8. I. Yavari, and M. Bayat Tetrahedron 59 2003 2001 2005
9. H. Choi, H. Hwang, J. Chin, E. Kim, J. Lee, S.-J. Nam, B.C. Lee, B.J. Rho, and H. Kang J. Nat. Prod. 74 2011 90 94
10. A. Aiello, E. Fattorusso, P. Luciano, A. Macho, M. Menna, and E. Munoz J. Med. Chem. 48 2005 3410 3416 and
11. A. Aiello, E. Fattorusso, P. Luciano, M. Menna, M.A. Calzado, E. Munoz, F. Bonadies, M. Guiso, M.F. Sanasi, G. Cocco, and R. Nicoletti Bioorg. Med. Chem. 18 2010 719 727
12. For a leading reference, see N.K. Utkina, V.A. Denisenko, and V.B. Krasokhin Tetrahedron Lett. 52 2011 3765 3768
13. C. Schiel, M. Oelgemoeller, J. Ortner, and J. Mattay Green. Chem. 3 2001 224 228 For reviews, see
14. K.T. Finley 5th ed. Quinones in Kirk-othmer Encyclopedia of Chemical Technology Vol. 21 2006 236-270 and
15. K. Maruyama, and A. Osuka Recent Advances in the Photochemistry of Quinones S. Patai, Z. Rappoport, Chem. Quinonoid Compd. Vol. 2 1988 759 878 Pt. 1
16. H. Iwamoto, A. Takuwa, K. Hamada, and R. Fujiwara J. Chem. Soc., Perkin Trans. 1 1999 575 581
17. K.A. Parker, and T.L. Mindt Org. Lett. 4 2002 4265 4268
18. L. Jurd Tetrahedron 33 1977 163 168
19. L.M. Bishop, M. Winkler, K.N. Houk, R.G. Bergman, and D. Trauner Chem. - Eur. J. 14 2008 5405 5408
20. A related enolization/electrocyclization has been suggested as the mechanism of the thermal isomerization of 2-demethylplastoquinone-3 to 7-demethylplastichromenol-2, see: B. Muckensturm, F. Diyani, J.-P. Reduron, and M. Hildenbrand Phytochemistry 45 1997 549 550
21. For a relevant review see: S.B. Ferreira, F. de C. da Silva, A.C. Pinto, D.T.G. Gonzaga, and V.F. Ferreira J. Heterocycl. Chem. 46 2009 1080 1097
22. L.M. Ambrosini, and T.H. Lambert ChemCatChem 2 2010 1373 1380
23. D.B. Ramachary, and S. Jain Org. Biomol. Chem. 9 2011 1277 1300
24. A.M. Walji, and D.W.C. MacMillan Synlett 2007 1477 1489
25. C.J. Chapman, and C.G. Frost Synthesis 2007 1 21
26. J.-C. Wasilke, S.J. Obrey, R.T. Baker, and G.C. Bazan Chem. Rev. 105 2005 1001 1020
27. The circular arrow notation in Scheme 4 is a convention introduced by Lambert; see: T.A. Cernak, and T.H. Lambert J. Am. Chem. Soc. 131 2009 3124 3125 and Ref. 14a. It is similar to notations for multicatalysis used in Refs. 14c-e
28. G.P. Ellis Chemistry of Heterocyclic Compounds 'Chromenes, Chromanones and Chromones' Vol. 31 1977 John New York, NY 11-141
29. S.-I. Takanashi, and K. Mori Liebigs Ann./Recl. 1997 825 838
30. A.P. Guzikowski, S.X. Cai, S.A. Espitia, J.E. Hawkinson, J.E. Huettner, D.F. Nogales, M. Tran, R.M. Woodward, E. Weber, and J.F.W. Keana J. Med. Chem. 39 1996 4643 4653
31. J. Zhu, R. Beugelmans, A. Bigot, G.P. Singh, and M. Bois-Choussy Tetrahedron Lett. 34 1993 7401 7404
32. D.R. McKean, G. Parrinello, A.F. Renaldo, and J.K. Stille J. Org. Chem. 52 1987 422 424
33. 4Pd catalyzed couplings by others; see, for example, K.S. Chan, and C.C. Mak Tetrahedron 50 1994 2003 2016
34. N.A. Bumagin, I.G. Bumagina, and I.P. Beletskaya Dokl. Akad. Nauk SSSR 274 1984 818 822
35. D.R. Williams, B.J. Myers, and L. Mi Org. Lett. 2 2000 945 948
36. J.M. Blatchly, R.J.S. Green, J.F.W. McOmie, and J.B. Searle J. Chem. Soc. C 1969 1353 1358
37. R.K. Norris, and S. Sternhell Aust. J. Chem. 19 1966 617
38. D.W. Cameron, and M.J. Crossley Aust. J. Chem. 31 1978 617 627
39. M.E. Jung, and J.A. Hagenah J. Org. Chem. 52 1987 1889 1902
40. C. Carmona, M. Galan, G. Angulo, M.A. Munoz, P. Guardado, and M. Balon Phys. Chem. Chem. Phys. 2 2000 5076 5083
41. C.H. Shunk, F.R. Koniuszy, E.L. Wong, N.R. Trenner, B.H. Arison, and K. Folkers Biochem. Biophys. Res. Commun. 2 1960 228 232
42. J. Mori, M. Iwashima, M. Takeuchi, and H. Saito Chem. Pharm. Bull. 54 2006 391 396
43. K.C. Nicolaou, P.K. Sasmal, and H. Wu J. Am. Chem. Soc. 126 2004 5493 5501
44. J.-P. Lumb, and D. Trauner Org. Lett. 7 2005 5865 5868
45. A.P.L. Alves, J.A.B.C. Junior, G.B.A. Slana, J.N. Cardoso, Q. Wang, R.S.C. Lopes, and C.C. Lopes Synth. Commun. 39 2009 3693 3709