Synthesis and Structural Reassignment of Plakinidone

Organic Letters

Volumn 17, Issue 20, 2015, Pages 5092-5095

  Xu, Ze Jun ^a   Tan, Dong Xing ^a   Wu, Yikang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; DIOXIN; LACTONE; PLAKINIDONE;

ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; MARINE BIOLOGY; NUCLEAR MAGNETIC RESONANCE; OXIDATION REDUCTION REACTION; SPONGE (PORIFERA); STEREOISOMERISM; SYNTHESIS;

ANIMALS; BIOLOGICAL PRODUCTS; DIOXINS; LACTONES; MARINE BIOLOGY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION; PORIFERA; STEREOISOMERISM;

EID: 84944930601     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02599     Document Type: Article

References (57)

1. Liu, D.-Z.; Liu, J.-K. Nat. Prod. Bioprospect. 2013, 3, 161-206 10.1007/s13659-013-0042-7
2. Dussault, P. H.; Liu, X. Org. Lett. 1999, 1, 1391-1393 10.1021/ol990954y
3. Murakami, N.; Kawanishi, M.; Itagaki, S.; Horii, T.; Kobayashi, M. Bioorg. Med. Chem. Lett. 2002, 12, 69-72 10.1016/S0960-894X(01)00673-4
4. Liu, H.-H.; Jin, H.-X.; Zhang, Q.; Wu, Y.-K.; Kim, H.-S.; Wataya, Y. Chin. J. Chem. 2005, 23, 1469-1473 10.1002/cjoc.200591469
5. Xu, C.; Raible, J. M.; Dussault, P. H. Org. Lett. 2005, 7, 2509-2511 10.1021/ol050291m
6. Ramirez, A.; Woerpel, K. A. Org. Lett. 2005, 7, 4617-4620 10.1021/ol051703u
7. Dai, P.; Trullinger, T. K.; Liu, X.; Dussault, P. H. J. Org. Chem. 2006, 71, 2283-2229 10.1021/jo0522254
8. Xu, C.; Schwartz, C.; Raible, J.; Dussault, P. H. Tetrahedron 2009, 65, 9680-9685 10.1016/j.tet.2009.09.068
9. Gemma, S.; Gabellieri, E.; Coccone, S. S.; Marti, F.; Taglialatela-Scafati, O.; Novellio, E.; Campiani, G.; Butini, S. J. Org. Chem. 2010, 75, 2333-2340 10.1021/jo1001559
10. Barnych, B.; Vatèle, J.-M. Org. Lett. 2012, 14, 564-567 10.1021/ol203185f
11. Barnych, B.; Fenet, B.; Vatèle, J.-M. Tetrahedron 2013, 69, 334-340 10.1016/j.tet.2012.10.022
12. Barnych, B.; Vatèle, J.-M. Tetrahedron 2012, 68, 3717-3724 10.1016/j.tet.2012.03.024
13. Gemma, S.; Kunjir, S.; Brindisi, M.; Novellio, E.; Campiani, G.; Butini, S. Tetrahedron Lett. 2013, 54, 1233-1235 10.1016/j.tetlet.2012.12.075
14. Kushlan, D. M.; Faulkner, D. J. J. Nat. Prod. 1991, 54, 1451-1454 10.1021/np50077a043
15. Hofheinz, W.; Schönholzer, P. Helv. Chim. Acta 1977, 60, 1367-1370 10.1002/hlca.19770600425
16. Gonzalez, A. G.; Martin, J. D.; Perez, C.; Rovirosa, J.; Tagle, B.; Clardy, J. Chem. Lett. 1984, 1649-1652 10.1246/cl.1984.1649
17. Li, Y.; Niu, S.; Sun, B.; Liu, S.; Liu, X.; Che, Y. Org. Lett. 2010, 12, 3144-3147 10.1021/ol101062f
18. Spence, J. T. J.; George, J. H. Org. Lett. 2011, 13, 5318-5321 10.1021/ol202181g
19. Mori, K.; Masuda, S.; Suguro, T. Tetrahedron 1981, 37, 1329-1340 10.1016/S0040-4020(01)92448-2
20. Enders, D.; Schuesseler, T. Tetrahedron Lett. 2002, 43, 3467-3470 10.1016/S0040-4039(02)00595-6
21. Schreiber, J.; Maag, H.; Hashimoto, N.; Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1971, 10, 330-331 10.1002/anie.197103301
22. Hon, Y.-S.; Chang, F.-J.; Lu, L.; Lin, W.-C. Tetrahedron 1998, 54, 5233-5246 10.1016/S0040-4020(98)00216-6
23. Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 573-576 10.1246/cl.1989.573
24. Barnych, B.; Vatèle, J.-M. Org. Lett. 2012, 14, 564-567 10.1021/ol203185f
25. Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J.; Kim, H.-S.; Wataya, Y. Tetrahedron 2001, 57, 5979-5989 10.1016/S0040-4020(01)00557-9
26. Ito, T.; Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J. Tetrahedron 2003, 59, 525-536 10.1016/S0040-4020(02)01556-9
27. Tokuyasu, T.; Kunikawa, S.; Abe, M.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Begum, K.; Wataya, Y. J. Org. Chem. 2003, 68, 7361-7367 10.1021/jo030107f
28. Gemma, S.; Marti, F.; Gabellieri, E.; Campiani, G.; Novellino, E.; Butini, S. Tetrahedron Lett. 2009, 50, 5719-5722 10.1016/j.tetlet.2009.07.137
29. Chen, H.-J.; Wu, Y.-K. Org. Lett. 2015, 17, 592-595 10.1021/ol503603t
30. O'Neill, P. M.; Pugh, M.; Davies, J.; Ward, S. A.; Park, B. K. Tetrahedron Lett. 2001, 42, 4569-4571 10.1016/S0040-4039(01)00791-2
31. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660 10.1016/0040-4020(78)80197-5
32. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156 10.1021/jo00170a070
33. Smith, A. B., III; Lin, Q. Y.; Doughty, V. A. Angew. Chem., Int. Ed. 2001, 40, 196-199 (periodinane/pyridine) 10.1002/1521-3773(20010105)40:1<196::AID-ANIE196>3.0.CO;2-T
34. Wirth, T. Angew. Chem., Int. Ed. 2001, 40, 2812-2814 (a review) 10.1002/1521-3773(20010803)40:15<2812::AID-ANIE2812>3.0.CO;2-X
35. Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D. J. Chem. Soc., Chem. Commun. 1987, 1625-1627 10.1039/c39870001625
36. Corey, E. J.; Suggs, W. Tetrahedron Lett. 1975, 16, 2647-2650 10.1016/S0040-4039(00)75204-X
37. Lucio Anelli, P. L.; Biffi, C.; Montanari, F. J. Org. Chem. 1987, 52, 2559-2562 10.1021/jo00388a038
38. DeMico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piancatelli, G. J. Org. Chem. 1997, 62, 6974-6977 10.1021/jo971046m
39. Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173-1175 10.1021/ol005792g
40. Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310-312 10.1021/jo9819032
41. Shibuya, M.; Tomizawa, M.; Suzuki, I.; Iwabuchi, Y. J. Am. Chem. Soc. 2006, 128, 8412-8413 10.1021/ja0620336
42. Bonini, C.; Di Fabio, R.; Sotgiu, G.; Cavagnero, S. Tetrahedron 1989, 45, 2895-2904 10.1016/S0040-4020(01)80118-6
43. Colvin, E. W.; Hamill, B. J. J. Chem. Soc., Perkin Trans. 1 1977, 869-874 10.1039/p19770000869
44. For known cases of carbine insertions into cyclic ketones, see: Liu, H.; Sun, C.; Lee, N.-K.; Henry, R. F.; Lee, D. Chem.-Eur. J. 2012, 18, 11889-11893 10.1002/chem.201201346
45. Seyferth, D.; Marmor, R. S.; Hilbert, P. J. Org. Chem. 1971, 36, 1379-1386 10.1021/jo00809a014
46. Akiyama, M.; Isoda, Y.; Nishimoto, M.; Kobayashi, A.; Togawa, D.; Hirao, N.; Kuboki, A.; Ohira, S. Tetrahedron Lett. 2005, 46, 7483-7485 10.1016/j.tetlet.2005.09.011
47. Paquette, L. A.; Owen, D. R.; Bibart, R. T.; Seekamp, C. K.; Kahane, A. L.; Lanter, J. C.; Corral, M. A. J. Org. Chem. 2001, 66, 2828-2834 10.1021/jo010026o
48. Nishikawa, Y.; Kitajima, M.; Takayama, H. Org. Lett. 2008, 10, 1987-1990 10.1021/ol800574v
49. Simmons, E. M.; Hardin, A. R.; Guo, X.; Sarpong, R. Angew. Chem., Int. Ed. 2008, 47, 6650-6653 10.1002/anie.200802203
50. Netherton, M. R.; Dai, C. Y.; Neuschutz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099-10100 10.1021/ja011306o
51. Matsuo, K.; Sakaguchi, Y. Heterocycles 1996, 43, 2553-2556 10.3987/COM-96-7632
52. Bühler, H.; Bayer, A.; Effenberger, F. Chem.-Eur. J. 2000, 6, 2564-2571 10.1002/1521-3765(20000717)6:14<2564::AID-CHEM2564>3.0.CO;2-F
53. Desmaele, D. Tetrahedron 1992, 48, 2925-2934 10.1016/S0040-4020(01)90974-3
54. Takaiwa, A.; Yamashita, K. Agric. Biol. Chem. 1983, 47, 429-430 10.1271/bbb1961.47.429
55. Small optical rotations measured at low concentrations (e.g., c = 0.01) may be unreliable, leading to confusion in the determination of absolute configurations. See, e.g.: Yong, K. W. L.; Barnych, B.; De Voss, J. J.; Vatèle, J.-M.; Garson, M. J. J. Nat. Prod. 2012, 75, 1792-1797 10.1021/np3005634
56. Varoglu, M.; Peters, B. M.; Crews, P. J. Nat. Prod. 1995, 58, 27-36 10.1021/np50115a003
57. Yong, K. W. L.; De Voss, J. J.; Hooper, J. N.; Garson, M. J. J. Nat. Prod. 2011, 74, 194-207 10.1021/np100620x