Diastereoselective synthesis of antiquorin and related polyoxygenated atisene-type diterpenes

Tetrahedron

Volumn 63, Issue 7, 2007, Pages 1664-1679

  Abad, Antonio ^a   Agulló, Consuelo ^a   Cuñat, Ana C ^a   de Alfonso Marzal, Ignacio ^a   Gris, Antonio ^a   Navarro, Ismael ^a   Ramírez de Arellano, Carmen ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Atisane; Carvone; Cyclopropane; Diels Alder reaction; Diterpene; Radical cleavage

Indexed keywords

18 HYDROXYATIS 16 ENE 3,14 DIONE; 3 BETA HYDROXYATIS 16 ENE 2,14 DIONE; ANTIQUORIN; ATIS 16 ENE 2,3,14 TRIONE; ATIS 16 ENE 3,14 DIONE; DITERPENE; HERBACEOUS AGENT; UNCLASSIFIED DRUG;

ARTICLE; CYCLOPROPANATION; DIELS ALDER REACTION; DRUG SYNTHESIS; EPIMER; EUPHORBIA; ISOLATION PROCEDURE; PRIORITY JOURNAL; STEREOCHEMISTRY;

ALNUS; EUPHORBIA;

EID: 33846076117     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.11.083     Document Type: Article

References (74)

1. Connolly J.D., and Hill R.A. Dictionary of Terpenoids. 1st ed. Vol. 2 (1991), Chapman and Hall, London pp 963-968
2. Zhi-Da M., Mizuno M., Tanaka T., Iinuma M., Guang-Yi X., and Qing H. Phytochemistry 28 (1989) 553-555
3. Shu S., Hai-Ming S., Liang J., Xue-Ting L., and Zhi-Da M. Zhongguo Tianran Yaowu 3 (2005) 31-33
4. Lal A.R., Cambie R.C., Rutledge P.S., Woodgate P.D., Rickard C.E.F., and Clark G.R. Tetrahedron Lett. 30 (1989) 3205-3208
5. Lal A.R., Cambie R.C., Rutledge P.S., and Woodgate P.D. Phytochemistry 29 (1990) 1925-1935
6. Prasad R., and Aalbersberg B. ACGC Chem. Res. Commun. 2 (1994) 7-10
7. Jia Z., Ding Y., Wang Q., and Liu Y. Phytochemistry 29 (1990) 2343-2345
8. Ding Y., Jia Z., Wang Q., Chen J., and Liu Y. Chin. J. Chem. 9 (1991) 131-135
9. Ng A.S. Phytochemistry 29 (1990) 662-664
10. Mbwambo Z.H., Lee S.K., Mshiu E.N., Pezzuto J.M., and Kinghorn A.D. J. Nat. Prod. 59 (1996) 1051-1055
11. Shi H.-M., Williams I.D., Sung H.H.-Y., Zhu H.-X., Ip N.Y., and Min Z.-D. Planta Med. 71 (2005) 349-354
12. Zhi-Da M., Bing W., Qi-Tai Z., Mizuno M., Iinuma M., and Tanaka T. Phytochemistry 29 (1990) 3952-3953
13. Cambie R.C., Clark G.R., Lal A.R., Rickard C.E.F., Rutledge P.S., and Woodgate P.D. Acta Crystallogr. C46 (1990) 2387-2389
14. Appendino G., Belloro E., Tron G.C., Jakupovic J., and Ballero M. Fitoterapia 71 (2000) 134-142
15. Gustafson K.R., Munro M.H.G., Blunt J.W., Cardellina II J.H., McMahon J.B., Gulakowski R.J., Cragg G.M., Cox P.A., Brinen L.S., Clardy J., and Boyd M.R. Tetrahedron 47 (1991) 4547-4554
16. Perry N.P., Burgess E.J., Baek S.-H., and Weavers R.T. Org. Lett. 3 (2001) 4243-4245
17. For recent examples of relevant biologically active atisanes, see:
18. Inden M., Kitamura Y., Kondo J., Hayashi K., Yanagida T., Takata K., Tsuchiya D., Yanagisawa D., Nishimura K., Taniguchi T., Shimohama S., Sugimoto H., and Akaike A. J. Neurochem. 95 (2005) 950-961
19. Ono, T.; Akaike, A.; Kenji, K.; Sugimoto, H. (Eisai Ltd., Japan). Jpn. Kokai Tokkyo Koho JP 2005289863, 20 October 2005.
20. Osakada F., Kawato Y., Kume T., Katsuki H., Sugimoto H., and Akaike A. J. Pharmacol. Exp. Ther. 311 (2004) 51-59
21. Akaike, A.; Sugimoto, H.; Nishizawa, Y.; Yonaga, M.; Asakawa, N.; Asai, N.; Mano, N.; Terauchi, T.; Doko, T. PCT Int. Appl. WO 2002088061, 7 November 2002.
22. For preparation of atisanes from other polycyclic terpenes, see:
23. Terauchi T., Asai N., Yonaga M., Kume T., Akaike A., and Sugimoto H. Tetrahedron Lett. 43 (2002) 3625-3628
24. Berettoni M., De Chiara G., Iacoangeli T., Lo Surdo P., Marini B.R., Montagnini di Mirabello L., Nicolini L., and Scarpelli R. Helv. Chim. Acta 79 (1996) 2035-2041
25. Garcia-Granados A., Dueñas J., Guerrero A., Martinez A., and Parra A. J. Nat. Prod. 59 (1996) 124-130
26. Fraga B.M., Guillermo R., and Hanson J. Phytochemistry 31 (1992) 503-506
27. Fraga B.M., Guillermo R., and Hanson J.R. J. Chem. Res., Synop. 4 (1990) 99-101
28. Campbell H.M., Gunn P.A., McAlees A.J., and McCrindle R. Can. J. Chem. 53 (1975) 20-25
29. Rodriguez B., and Valverde S. Chem. Ind. (London) (1974) 1010-1011
30. Campbell H.M., Gunn P.A., McAlees A.J., and McCrindle R. Can. J. Chem. 51 (1973) 4167-4174
31. Baker K.M., Briggs L.H., Buchanan J.G.St.C., Cambie R.C., Davis B.R., Hayward R.C., Long G.A.S., and Rutledge P.S. J. Chem. Soc., Perkin Trans. 1 (1972) 190-194
32. Coates R.M., and Bertram E.F. J. Org. Chem. 36 (1971) 2625-2631
33. Coates R.M., and Bertram E.F. J. Chem. Soc., Chem. Commun. (1969) 797-798
34. Appleton R.A., Gunn P.A., and McCrindle R.A. J. Chem. Soc., Chem. Commun. (1968) 1131-1132
35. Zalkow L.H., and Oehlschlager A.C. J. Org. Chem. 32 (1967) 808-810
36. Hugel G., Lods L., Mellor J.M., and Ourisson G. Bull. Soc. Chim. Fr. 10 (1965) 2894-2902
37. Bell R.A., Ireland R.E., and Partyka R.A. J. Org. Chem. 31 (1966) 2530-2561
38. Goldsmith D. In: ApSimon J. (Ed). The Total Synthesis of Tri- and Tetracyclic Diterpenes. The Total Synthesis of Natural Products Vol. 8 (1992), Wiley, New York, NY 115-118
39. Ihara M., Toyota M., Fukumoto K., and Kametani T. Tetrahedron Lett. 26 (1985) 1537-1540
40. Ihara M., Toyota M., Fukumoto K., and Kametani T. Tetrahedron Lett. 25 (1984) 2167-2170
41. Ihara M., Toyota M., Fukumoto K., and Kametani T. Tetrahedron Lett. 25 (1984) 3235-3238
42. Toyota M., Yokota M., and Ihara M. Tetrahedron Lett. 40 (1999) 1551-1554
43. Ihara M., Toyota M., Fukumoto K., and Kametani T. J. Chem. Soc., Perkin Trans. 1 (1986) 2151-2161
44. Toyota M., Wada T., and Ihara M. J. Org. Chem. 65 (2000) 4565-4570
45. Toyota M., Wada T., Fukumoto K., and Ihara M. J. Am. Chem. Soc. 120 (1998) 4916-4925
46. Toyota M., Yokota M., and Ihara M. J. Am. Chem. Soc. 123 (2001) 1856-1861
47. Toyota M., Yokota M., and Ihara M. Org. Lett. 1 (1999) 1627-1629
48. Toyota M., Asano T., and Ihara M. Org. Lett. 7 (2005) 3929-3932
49. Abad A., Agulló C., Cuñat A.C., de Alfonso Marzal I., Navarro I., and Gris A. Tetrahedron 62 (2006) 3266-3283
50. Abad A., Agulló C., Cuñat A.C., and Navarro I. Tetrahedron Lett. 42 (2001) 8965-8968
51. Corbel B., Medinger L., Haelters J.P., and Sturtz G. Synthesis (1985) 1048-1051
52. Craig D. Chem. Soc. Rev. 16 (1987) 187-238
53. Roush W.R. In: Curran D.P. (Ed). Advances in Cycloaddition Vol. 2 (1990), JAI, Greenwich, CT 91-146
54. Takao K., Munakata R., and Tadano K. Chem. Rev. 105 (2005) 4779-4807
55. Regitz M. Synthesis (1972) 351-373
56. Danheiser R.L., Miller R.F., Brisbois R.G., and Park S.Z. J. Org. Chem. 55 (1990) 1959-1964
57. Vedejs E., Engler D.A., and Telschow J.E. J. Org. Chem. 55 (1990) 3715-3717
58. Rubottom G.M., Vazquez M.A., and Pelegrina D.R. Tetrahedron Lett. (1974) 4319-4322
59. Saito S., Yamazaki S., Shiozawa M., and Yamamoto H. Synlett (1999) 581-583
60. Wehrli F.W., Marchand A.P., and Wehrli S. Interpretation of Carbon-13 NMR Spectra (1988), Wiley, New York, NY p 54
61. Omoto M., Kato N., Sogon T., and Moei A. Tetrahedron Lett. 42 (2001) 939-941
62. The isomerisation of the C15-C16 double bond was first attempted photochemically without success, see:. Kropp P.J., Reardon E.J., Gaibel Z.L.F., Williard K.F., and Hattaway J.H. J. Am. Chem. Soc. 95 (1973) 7058-7067
63. Yajima A., and Mori K. Eur. J. Org. Chem. (2000) 4079-4091
64. For related opening of silyl cyclopropyl ethers to give β-bromo ketones, see:
65. Murai S., Seki Y., and Sonoda N. J. Chem. Soc., Chem. Commun. (1974) 1032-1033
66. Gibson D.H., and Charles H.D. Chem. Rev. 74 (1974) 605-623
67. Hutchins R.O., and Taffer I.M. J. Org. Chem. 48 (1983) 1360-1362
68. Alexander J., Renyer M.L., and Veerapanane H. Synth. Commun. 25 (1995) 3875-3881
69. Chan T.H., and Gingras M. Tetrahedron Lett. 30 (1989) 279-282
70. We have found that this procedure is very efficient for the preparation of different types of alcohols from halides under very mild conditions, see:. Abad A., Agulló C., Cuñat A.C., and Navarro I. Synthesis (2005) 3355-3361
71. See, for example:
72. Takaishi Y., Miyagi K., Kawazoe K., Nakano K., Li K., and Duan H. Phytochemistry 45 (1997) 975-978
73. Nuñez M.J., Reyes C.P., Jiménez I.A., Moujir L., and Bazzocchi I.L. J. Nat. Prod. 68 (2005) 1018-1021
74. Vedejs E., and Larsen S. Org. Synth. Coll. 7 (1990) 277-282