Synthetic Studies of Nitrogen-containing Terpenes Originated from Marine Organism Using Sigmatropic Rearrangement and Ritter Reaction

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 55, Issue 4, 1997, Pages 281-289

  Ichikawa, Yoshiyasu ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Allyl cyanate; Allyl sulfinate; Allyl xanthate; Biomimetic synthesis; Marine natural products; Ritter reaction; Sigmatropic rearrangement; Terpen

Indexed keywords

BIOSYNTHESIS; CONFORMATIONS; MARINE BIOLOGY; MOLECULAR STRUCTURE;

AGELASIDINE A; ALLYL CYANATE; ALLYL SULFINATE; ALLYL XANTHATE; BIOMIMETIC SYNTHESIS; HETERO-CLAISEN REARRANGEMENT; MARINE ORGANISMS; RITTER REACTION; SIGMATROPIC REARRANGEMENT; TERPENES;

ORGANIC COMPOUNDS;

EID: 0031118439     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.55.281     Document Type: Article

References (56)

1. (a) H. Nakamura, H. Wu, J. Kobayashi, Y. Ohizumi, Y. Hirata, T. Higasijima, T. Miyazawa, Tetrahedron Lett., 24, 4105 (1983);
2. (b) H. Nakamura, H. Wu, J. Kobayashi, M. Kobayashi, Y. Ohizumi, Y. Hirata, J. Org. Chem., 50, 2494 (1985);
3. R.J. Capon, D.J. Faulkner, J. Am. Chem. Soc., 106, 1819 (1984)
4. (a) F.R.J. Ferrrier, N. Vethaviyasar, J. Chem. Soc., Chem. Commun., 1970, 1385;
5. (b) J.E. Baldwin, G. Hofle, J. Am. Chem. Soc., 1971, 6307;
6. (c) K. Harano, T. Taguchi, Chem. Pharm. Bull., 20, 2348 (1972);
7. idem, ibid., 20, 2348 (1972)
8. H.S. Schulltz, H.B. Freyermuth, J. Org. Chem., 28, 1140 (1960)
9. M. Bodansz, M.A. Ondetti, C.A. Birkhimer, P.L. Thomas, J. Am. Chem. Soc., 86, 4452 (1964)
10. M. Bodanszky, Peptide Chemistry, Springer- Verlag, Berlin, Heidelberg, 1988, p.94
11. Y. Ichikawa, Tetrahedron Lett., 29, 4957 (1988)
12. S. Thea, G. Cevasxo, Tetrahedron Lett., 43, 5139 (1987)
13. (a) K. Hiroi, R. Kitayama, S. Sato, J. Chem. Soc., Chem. Commun., 1983, 1473;
14. (b) A.C. Cope, D.E. Morrison, L. Field, J. Am. Chem. Soc., 72, 59 (1950)
15. J.E. Baldwin, W.F. Erickson, R.E. Hackler, R.M. Scott, J. Chem. Soc., Chem. Commun., 1970, 576
16. (a) see the reference 2b;
17. (b) H. Iio, K. Asao, T. Tokoroyama, J. Chem. Soc., Chem. Commun., 1985, 774;
18. M. Asano, H. Iio, T. Tokoroyama, Chem. Lett., 1989, 1813
19. Y. Ichikawa, T. Kashiwagi, N. Urano, J. Chem. Soc., Chem. Commun., 1989, 987
20. B.W. Sullivan, D.J. Faulkner, K.T. Okamoto, M.H.M. Chen, J. Clardy, J. Org. Chem., 51, 5143 (1986)
21. I. Kitagawa, N. Yoshioka, C. Kamba, M. Yoshikawa, Y. Hamamoto, Chem. Pharm. Bull., 35, 928 (1987)
22. N.K. Gulavita, E.D. deSilva, M.R. Hagadone, P. Karuso, P.J. Scheuer, G.D. VanDuyne, J. Clardy, J. Org. Chem., 51, 5136 (1986)
23. L.E. Overman, J. Am. Chem. Soc., 96, 597 (1974);
24. L.E. Overman, ibid., 98, 2901 (1976)
25. H.C. Brown, K.J. Murray, J.A. Snover, G. Zweifel, J. Am. Chem. Soc., 82, 4233 (1960);
26. H.C. Brown, G. Zweifel, ibid., 83, 1241 (1961)
27. L.I. Kimen, D.J. Cota, Org. React., 17, 213 (1969)
28. (a) C.J.R. Fookes, M.J. Garson, J.K. MacLeod, B.W. Skelton, A.H. White, J. Chem. Soc., Perkin Trans. 1, 1988, 1003;
29. (b) M.J. Gason, Natural Product Reports, 6, 143 (1989)
30. W.S. Johson; see the reference, W.S. Johnson, M.B. Gravestock, R.J. Parry, R.F. Myers, T.A. Bryson, D.H.H. Miles, J. Am. Chem. Soc., 93, 4330 (1971)
31. Y. Ichikawa, Chem. Lett., 1990, 1347
32. H. Nakamura, J. Kobayashi, Y. Ohizumi, Tet rahedron Lett., 25, 5401 (1984)
33. N.K. Gulavita, E.D. de Silva, M.R. Hagadone, P. Karuso, P.J. Scheuer, G.D. van Duyne, J. Clardy, J. Org. Chem., 51, 5136 (1986)
34. B.J. Burreson, C. Christophersen, P.J. Scheuer, Tetrahedron, 31, 2018 (1975)
35. P.J. Kocienski, B. Lythgoe, I. Waterhouse, J. Chem. Soc., Perkin Trams. 1, 1980, 1045
36. J.E. Baldwin, I.A. O'Neil, Synlett, 1990, 603
37. (a) Y. Ichikawa, Synlett, 1991, 715;
38. (b) idem, J. Chem. Soc., Perkin Trans. 1, 1992, 2135
39. P.A. Smith, D.W. Emerson, J. Am. Chem. Soc., 82, 3076 (1960)
40. (a) R.J. Ferrier, N. Vethaviyasar, J. Chem. Soc., Chem. Commun., 1970, 1385;
41. (b) R.J. Ferrier, N. Prasad, J. Chem. Soc. (C), 1969, 570
42. (a) C. Christophersen, A. Holms, Acta Chem. Scand., 24, 1512 (1970);
43. (b) idem, ibid., 24, 1852 (1970);
44. K.A. Jensen, A. Holm, The Chemistry of Cyanates and Their Thio Derivatives 1; Patai, S., Eds., John Wiley & Sons, 1977, 569
45. D. Martin, M. Bauer, Organic Synthesis Collective Volume 7, 435 (1990)
46. L.E. Overmann, M. Kakimoto, J. Org. Chem., 43, 4564 (1978)
47. K.A. Jensen, A. Holm, Acta Chem. Scand., 18, 2417 (1964)
48. Y. Ichikawa, Synlett, 1991, 238
49. (a) J.E. Baldwin, I.A. O'Neil, Synlett, 1990, 603;
50. (b) R. Apple, R. Kleinstruck, K. Ziehn, Angew. Chem., Int. Ed. Engl., 10, 132 (1971)
51. (a) B.J. Burreson, P.J. Scheuer, J. Chem. Soc., Chem. Commun., 1974, 1035;
52. (b) B.J. Burreson, C. Chritophersen, P.J. Scheuer, Tetrahedron, 31, 2015 (1975)
53. Y. Ichikawa, H. Yamazaki, M. Isobe, J. Chem. Soc., Perkin Trans, 1, 1993, 2429