Creation of quarternary stereocentres via [3,3]-sigmatropic rearrangement of allylic thiocyanates. A synthetic approach to (+)-myriocin

Tetrahedron Asymmetry

Volumn 17, Issue 12, 2006, Pages 1875-1882

  Gonda, Jozef ^a   Martinková, Miroslava ^a   Raschmanová, Jana ^a   Balentová, Eva ^a  

^a P J AFÁRIK UNIVERSITY   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CARBOXYLIC ACID DERIVATIVE; GLUCOSE; THERMOZYMOCIDIN; THIOCYANIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; PHASE TRANSITION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 33746404651     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.06.032     Document Type: Article

References (56)

1. Overman L.E. J. Am. Chem. Soc. 96 (1974) 597-599
2. Ikariya T., Ishikawa Y., Hirai K., and Yoshikawa S. Chem. Lett. (1982) 1815-1821
3. Overman L.E. Angew. Chem., Int. Ed. Engl. 23 (1984) 579-585
4. Schenck T.G., and Bosnich B. J. Am. Chem. Soc. 107 (1985) 2058-2066
5. Savage I., and Thomas E.J. J. Chem. Soc., Chem. Commun. (1989) 717-719
6. Metz P., Mues C., and Schoop A. Tetrahedron 48 (1992) 1071-1080
7. Mehmandoust M., Petit M., and Larcheveque Y. Tetrahedron Lett. 33 (1992) 4313-4316
8. Gonda J., Helland A.-C., Ernst B., and Bellus D. Synthesis (1993) 729-734
9. Chen A., Savage I., Thomas E.J., and Wilson P.D. Tetrahedron Lett. 34 (1993) 6769-6772
10. Calter M., Hollis T.K., Overman L.E., Ziller J., and Zipp G.G. J. Org. Chem. 62 (1997) 1449-1456
11. Overman L.E., and Zipp G.G. J. Org. Chem. 62 (1997) 2288-2291
12. Hollis T.K., and Overman L.E. Tetrahedron Lett. 38 (1997) 8837-8840
13. Nishikawa T., Asai M., Ohyabu N., Yamamoto N., Fukuda Y., and Isobe M. Tetrahedron 57 (2001) 3875-3883
14. Johansen M., and Jorgensen K.A. Chem. Rev. 98 (1988) 1689-1708
15. Cativiela C., and Diaz-de-Vilegas M.D. Tetrahedron: Asymmetry 9 (1988) 3517-3599
16. Petranyi G., Ryder N.S., and Stutz A. Science 224 (1984) 1239-1241
17. Burges K., and Ohlmeyer M.J. J. Org. Chem. 56 (1991) 1027-1036
18. Vedejs E., and Gingras N. J. Am. Chem. Soc. 116 (1994) 579-588
19. Johnson T.A., Curtis M.D., and Break P. J. Am. Chem. Soc. 123 (2001) 1004-1005
20. Gonda J., Závacká E., Buděšínský M., Císařová I., and Podlaha J. Tetrahedron Lett. 41 (2000) 525-529
21. Gonda J., Martinková M., Walko M., Závacká E., Buděšínský M., and Císařová I. Tetrahedron Lett. 42 (2001) 4401-4405
22. Gonda J., Martinková M., and Imrich J. Tetrahedron 58 (2002) 1611-1616
23. Gonda J. Angew. Chem., Int. Ed. 43 (2004) 3516-3524
24. For total synthesis of myriocin and synthetic approaches:. Just G., and Payette D.R. Tetrahedron Lett. 21 (1980) 3219-3222
25. Banfi L., Beretta M.G., Colombo L., Gennari C., and Scolastico C. J. Chem. Soc., Perkin Trans. 1 (1983) 1613-1619
26. Yoshikawa M., Yokokawa Y., Okuno Y., and Murakami N. Tetrahedron 51 (1995) 6209-6228
27. Sano S., Kobayashi Y., Kondo T., Takebayashi M., Maruyama S., Fujita T., and Nagao Y. Tetrahedron Lett. 36 (1995) 2097-2100
28. Hatakeyama S., Yoshida M., Esumi T., Iwabuchi Y., Irie H., Kawamoto T., Yamada H., and Nishizawa M. Tetrahedron Lett. 38 (1997) 7887-7890
29. Rao A.V.R., Gurjar M.K., Devi T.R., and Kumar K.R. Tetrahedron Lett. 34 (1993) 1653-1656
30. Deloisy S., Thang T.T., Olesker A., and Lukacs G. Tetrahedron Lett. 35 (1994) 4783-4786
31. For total syntheses of sphingofungin E:. Kobayashi S., Hayashi T., Iwamoto S., Furuta T., and Matsumura M. Synlett (1996) 672-674
32. Kobayashi S., Matsumura M., Furuta T., Hayashi T., and Iwamoto S. Synlett (1997) 301-303
33. Kobayashi S., Furuta T., Hayashi T., Nishijima M., and Hanada K. J. Am. Chem. Soc. 120 (1998) 908-919
34. Kobayashi S., and Furuta T. Tetrahedron 54 (1998) 10275-10294
35. For total syntheses of sphingofungin D:. Chida N., Ikemoto H., Noguchi A., Amano S., and Ogawa S. Nat. Prod. Lett. 6 (1995) 295-300
36. Mori K., and Otaka K. Tetrahedron Lett. 35 (1994) 9207-9210
37. Mori K. Eur. J. Org. Chem. (1999) 1795-1802
38. Lee C.-B., and Trost B.M. J. Am. Chem. Soc. 123 (2001) 12191-12201
39. Wang B., Yu X.-M., and Lin G.-Q. Synlett (2001) 904-906
40. Nakamura T., and Shiozaki M. Tetrahedron Lett. 42 (2001) 2701-2704
41. For total syntheses of sphingofungin F:. Trost B.M., and Lee C.B. J. Am. Chem. Soc. 120 (1998) 6818-6819
42. Liu D.-G., Wang B., and Lin G.-Q. J. Org. Chem. 65 (2000) 9114-9119
43. Tronchet J.M., and Gentile B. Carbohydr. Res. 44 (1975) 23-35
44. Gonda J., and Bednáriková M. Tetrahedron Lett. 38 (1997) 5569-5572
45. Guner V., Khuong K.S., Leach A.G., Lee P.S., Bartberger M.D., and Houk K.N. J. Phys. Chem. A 107 (2003) 11445-11459 and references cited therein
46. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
47. Perdew J.R., and Wang Y. Phys. Rev. B 45 (1992) 13244-13249
48. Tomasi J., and Persico M. Chem. Rev. 94 (1994) 2027-2094
49. Simkin B.Y., and Sheikhet I. Quantum Chemical and Statistical Theory of Solutions-A Computational Approach (1995), Ellis Horwood, London
50. Cancés E., Mennucci B., and Tomasi J. J. Chem. Phys. 107 (1997) 3032-3041
51. Mennucci B., and Tomasi J. J. Chem. Phys. 106 (1997) 5151-5158
52. Mennucci B., Cancés E., and Tomasi J. J. Phys. Chem. B 101 (1997) 10506-10517
53. Tomasi J., Mennucci B., and Cancés E. J. Mol. Struct. (THEOCHEM) 464 (1999) 211-226
54. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery Jr. J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 03, Revision C.2 (2003), Gaussian, Pittsburgh, PA
55. Kotani M., Shigetomi Y., Imada M., and Oki M. Heteroatom Chem. 8 (1997) 35-43
56. Iliceto A., Fava A., Mazzucato U., and Radici P. Gazz. Chim. Ital. 11 (1960) 27-32