Total syntheses of secalonic acids A and D

Angewandte Chemie - International Edition

Volumn 53, Issue 12, 2014, Pages 3107-3110

  Qin, Tian ^a   Porco Jr , John A ^a  

^a Boston University   (United States)

Author keywords

dimerization; kinetic resolution; natural products; stannanes; total synthesis

Indexed keywords

CATALYSIS; COPPER; DIMERIZATION; KINETICS; MONOMERS;

CONCISE SYNTHESIS; CORE STRUCTURE; HOMODIMERIZATION; KINETIC RESOLUTION; METHOXYMETHYL; NATURAL PRODUCTS; STANNANES; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

BIOLOGICAL PRODUCT; SECALONIC ACID; XANTHONE DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BIOLOGICAL PRODUCTS; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM; XANTHONES;

EID: 84896376250     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201311260     Document Type: Article

References (55)

1. S. Bräse, A. Encinas, J. Keck, C. F. Nising, Chem. Rev. 2009, 109, 3903-3990
2. K.-S. Masters, S. Bräse, Chem. Rev. 2012, 112, 3717-3776.
3. For the isolation of secalonic acid A, see:, B. Franck, E. M. Gottschalk, U. Ohnsorge, G. Baumann, Angew. Chem. 1964, 76, 438-439
4. Angew. Chem. Int. Ed. Engl. 1964, 3, 441-442
5. B. Franck, G. Baumann, U. Ohnsorge, Tetrahedron Lett. 1965, 6, 2031-2037
6. B. Franck, E. M. Gottschalk, U. Ohnsorge, F. Hüper, Chem. Ber. 1966, 99, 3842-3862; First the isolation of secalonic acid D, see
7. P. S. Steyn, Tetrahedron 1970, 26, 51-57.
8. J. Zhang, L. Tao, Y. Liang, Y. Yan, C. Dai, X. Xia, Z. She, Y. Lin, L. Fu, Cell Cycle 2009, 8, 2444-2450
9. R. Hong, Pharm. Biol. 2011, 49, 796-799.
10. A. Zhai, Y. Zhang, X. Zhu, J. Liang, X. Wang, Y. Lin, R. Chen, Neurochem. Int. 2011, 58, 85-91.
11. H. Kikuchi, M. Isobe, M. Sekiya, Y. Abe, T. Hoshikawa, K. Ueda, S. Kurata, Y. Katou, Y. Oshima, Org. Lett. 2011, 13, 4624-4627
12. H. Kikuchi, M. Isobe, S. Kurata, Y. Katou, Y. Oshima, Tetrahedron 2012, 68, 6218-6223.
13. M. Stewart, R. J. Capon, J. M. White, E. Lacey, S. Tennant, J. H. Gill, M. P. Shaddock, J. Nat. Prod. 2004, 67, 728-729.
14. T. Qin, R. P. Johnson, J. A. Porco, Jr., J. Am. Chem. Soc. 2011, 133, 1714-1717.
15. B. Lesch, S. Bräse, Angew. Chem. 2004, 116, 118-120
16. Angew. Chem. Int. Ed. 2004, 43, 115-118
17. C. F. Nising, U. K. Ohnemüller, S. Bräse, Angew. Chem. 2005, 117, 313-315
18. Angew. Chem. Int. Ed. 2006, 45, 307-309
19. U. K. Ohnemüller (née Schmid), C. F. Nising, M. Nieger, S. Bräse, Eur. J. Org. Chem. 2006, 1535-1546
20. C. F. Nising, A. Friedrich, S. Bräse, Synlett 2007, 2987-2990
21. U. K. Ohnemüller, C. F. Nising, A. Encinas, S. Bräse, Synthesis 2007, 2175-2185
22. E. M. C. Gérared, S. Bräse, Chem. Eur. J. 2008, 14, 8086-8089
23. N. Volz, M. C. Bröhmer, M. Nieger, S. Bräse, Synlett 2009, 550-553
24. M. C. Bröhmer, E. B. Bourcet, M. Nieger, S. Bräse, Chem. Eur. J. 2011, 17, 13706-13711
25. A. M. Linsenmeier, S. Bräse, Eur. J. Org. Chem. 2012, 6455-6459
26. A. C. Meister, M. Nieger, S. Bräse, Chem. Eur. J. 2013, 19, 10836-10839.
27. K. C. Nicolaou, A. Li, Angew. Chem. 2008, 120, 6681-6684
28. Angew. Chem. Int. Ed. 2008, 47, 6579-6582.
29. L. F. Tietze, D. A. Spiegl, F. Stecker, J. Major, C. Raith, C. Große, Chem. Eur. J. 2008, 14, 8956-8963
30. L. F. Tietze, S. Jackenkroll, C. Raith, D. A. Spiegl, J. R. Reiner, M. Claudia, O. Campos, Chem. Eur. J. 2013, 19, 4876-4882
31. L. F. Tietze, L. Ma, J. R. Reiner, S. Jackenkroll, S. Heidemann, Chem. Eur. J. 2013, 19, 8610-8614.
32. I. Kurobane, L. C. Vining, A. G. McInnes, J. A. Walter, J. L. C. Wright, Tetrahedron Lett. 1978, 19, 1379-1382
33. I. Kurobane, L. C. Vining, J. Antibiot. 1979, 32, 1256-1266; for the possible relationship between tetrahydroxanthones and chromone lactones, see
34. N. Tabata, H. Tomada, K. Matsuzaki, S. Omura, J. Am. Chem. Soc. 1993, 115, 8558-8564
35. N. Tabata, H. Tomoda, Y. Iwai, S. Omura, J. Antibiot. 1996, 49, 267-271.
36. For synthesis of an isomer of the chromone lactone dimer paecilin A, see:, L. F. Tietze, L. Ma, S. Jackenkroll, J. R. Reiner, J. Hierold, B. Gnanaprakasam, S. Heidemann, Heterocycles 2014, 88, 1101-1119.
37. For a review on aryl-aryl bond formation, see:, J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1470.
38. R. C. Cambie, P. S. Rutledge, T. Smith-Palmer, P. D. Woodgate, J. Chem. Soc. Perkin Trans. 1 1976, 1161-1164.
39. S. Kajigaeshi, T. Kakinami, H. Yamasaki, S. Fujisaki, M. Kondo, T. Okamoto, Chem. Lett. 1987, 2109-2112.
40. M. Piber, A. E. Jensen, M. Rottlander, P. Knochel, Org. Lett. 1999, 1, 1323-1326
41. J.-F. Nguefack, V. Bolitt, D. Sinou, Tetrahedron Lett. 1996, 37, 5527-5530
42. N. A. Powell, S. D. Rychnovsky, Tetrahedron Lett. 1996, 37, 7901-7904.
43. X. Han, B. M. Stoltz, E. J. Corey, J. Am. Chem. Soc. 1999, 121, 7600-7605.
44. E. Piers, J. G. K. Yee, P. L. Gladstone, Org. Lett. 2000, 2, 481-484
45. K. Nabatame, M. Hirama, M. Inoue, Heterocycles 2008, 76, 1011-1016; for copper-chloride-mediated couplings of vinyl stannanes, see
46. E. Piers, M. A. Romero, J. Am. Chem. Soc. 1996, 118, 1215-1216; for copper-nitrate-mediated arylstannane coupling, see
47. S. Ghosal, G. P. Luke, K. S. Kyler, J. Org. Chem. 1987, 52, 4296-4298; For catalytic copper(II)-chloride-mediated stannane coupling, see
48. S.-K. Kang, T.-G. Baik, X. H. Jiao, Y.-T. Lee, Tetrahedron Lett. 1999, 40, 2383-2384.
49. For a review on oxidation of organocuprates, see:, D. S. Surry, D. R. Spring, Chem. Soc. Rev. 2006, 35, 218-225.
50. V. B. Birman, X. Li, Org. Lett. 2006, 8, 1351-1354
51. V. B. Birman, X. Li, Org. Lett. 2008, 10, 1115-1118
52. X. Li, H. Jiang, E. W. Uffman, L. Guo, Y. Zhang, X. Yang, V. B. Birman, J. Org. Chem. 2012, 77, 1722-1737.
53. For a recent review of organocatalytic, enantioselective acyl transfer, see:, C. E. Müller, P. R. Schreiner, Angew. Chem. 2011, 123, 6136-6167
54. Angew. Chem. Int. Ed. 2011, 50, 6012-6042.
55. CCDC 961591 [(-)- 17 }, 961692 [(+)- 31 ] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.