An enantiospecific approach to pinguisanes from (R)-carvone. Total synthesis of (+)-pinguisenol

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 16, 2000, Pages 2583-2589

  Srikrishna, Adusumilli ^a   Vijaykumar, Dange ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALKYLATION; CARBOHYDRATES; ESTERS; KETONES; OXIDATION; REDUCTION; STEREOCHEMISTRY;

INTRAMOLECULAR CYCLOPROPANATION;

SYNTHESIS (CHEMICAL);

EID: 0034699188     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b004770h     Document Type: Article

References (100)

1. B. M. Fraga, Nat. Prod. Rep., 1985, 2, 147;
2. B. M. Fraga, Nat. Prod. Rep., 1986, 3, 273;
3. B. M. Fraga, Nat. Prod. Rep., 1987, 4, 473;
4. B. M. Fraga, Nat. Prod. Rep., 1988, 5, 497;
5. B. M. Fraga, Nat. Prod. Rep., 1990, 7, 61;
6. B. M. Fraga, Nat. Prod. Rep., 1992, 9, 217, 557;
7. B. M. Fraga, Nat. Prod. Rep., 1993, 10, 397;
8. B. M. Fraga, Nat. Prod. Rep., 1994, 11, 533;
9. B. M. Fraga, Nat. Prod. Rep., 1995, 12, 303;
10. B. M. Fraga, Nat. Prod. Rep., 1996, 13, 307;
11. B. M. Fraga, Nat. Prod. Rep., 1997, 14, 145;
12. B. M. Fraga, Nat. Prod. Rep., 1998, 15, 73;
13. B. M. Fraga, Nat. Prod. Rep., 1999, 16, 21, 711
14. G. W. Gribble, in Progress in the Chemistry of Organic Natural Products, eds., W. Herz, G. W. Kirby, R. E. Moore, W. Steglich and Ch. Tamm, Springer, Vienna, New York, 1996, vol. 68, pp. 1-87
15. S. B. Christensen, A. Andersen and U. W. Smitt, in Progress in the Chemistry of Organic Natural Products, eds. W. Herz, G. W. Kirby, R. E. Moore, W. Steglich and Ch. Tamm, Springer, Vienna, New York, 1997, vol. 71, pp. 129-167.
16. Y. Asakawa, in Progress in the Chemistry of Organic Natural Products, eds. W. Herz, G. W. Kirby, R. E. Moore, W. Steglich and Ch. Tamm, Springer, Vienna, New York, 1995, vol. 65, pp. 1-296.
17. (a) Y. Asakawa, M. Toyota and T. Aratani, Tetrahedron Lett., 1976, 3619
18. (b) V. Benesova, Z. Samek, V. Herout and F. Sorm, Collect. Czech. Chem. Commun., 1969, 34, 582
19. (c) V. Benesova, V. Herout and F. Sorm, Collect. Czech. Chem. Commun., 1969, 34, 1810
20. (d) S. M. Krutov, Z. Samek, V. Benesova and V. Herout, Phytochemistry, 1973, 12, 1405
21. (e) A. Corbella, P. Gariboldi, G. Jommi, F. Orsini, A. DeMarco and A. Immirzi, J. Chem. Soc., Perkin Trans. 1, 1974, 1875
22. (f) Y. Asakawa, M. Toyota, M. Uemoto and T. Aratani, Phytochemistry, 1976, 15, 1929
23. (g) Y. Asakawa, M. Toyota and T. Takemoto, Phytochemistry, 1978, 17, 457
24. (h) Y. Asakawa, M. Toyota, T. Takemoto and C. Suire, Phytochemistry, 1979, 18, 1349
25. (i) Y. Asakawa, M. Toyota, M. Kano and T. Takemoto, Phytochemistry, 1980, 19, 2651
26. (j) Y. Asakawa, M. Toyota, T. Takemoto and R. Mues, Phytochemistry, 1981, 20, 2695
27. (k) Y. Asakawa, M. Toyota and T. Takemoto, Phytochemistry, 1981, 20, 257
28. (l) Y. Asakawa, M. Toyota, R. Takeda, G. Suire and T. Takemoto, Phytochemistry, 1981, 20, 725
29. (m) Y. Asakawa, R. Matsuda and C. Suire, Phytochemistry, 1981, 20, 1427
30. (n) R. Takeda, H. Naoki, T. Iwashita and Y. Hirose, Tetrahedron Lett., 1981, 22, 5307
31. (o) Y. Fukuyama, M. Tori, M. Wakamatsu and Y. Asakawa, Phytochemistry, 1988, 27, 3557
32. (p) M. Toyota, F. Nagashima and Y. Asakawa, Phytochemistry, 1989, 28, 1661
33. (q) M. Toyota, H. Koyama, T. Hashimoto and Y. Asakawa, Chem. Pharm. Bull, 1995, 43, 714
34. (r) M. S. Buchanan, J. D. Connolly and D. S. Rycroft, Phytochemistry, 1996, 43, 1249
35. (s) D. S. Rycroft and W. J. Cole, J. Chem. Res. (S), 1998, 600
36. (t) T. Hashimoto, H. Irita, M. Tanaka, S. Takaoka and Y. Asakawa, Tetrahedron Lett., 1998, 39, 2977
37. (u) H. Tazaki, F. Ishikawa, H. Soutome and K. Nabeta, Phytochemistry, 1998, 48, 851
38. (v) M. Bungert, J. Gabler, K. P. Adam, J. Zapp and H. Becker, Phytochemistry, 1998, 49, 1079.
39. D. Schinzer and K. Ringe, Tetrahedron, 1996, 52, 7475.
40. For synthesis of other pinguisanes see: S. Bernasconi, P. Gariboldi, G. Jommi, S. Montanari and M. Sisti, J. Chem. Soc., Perkin Trans. 1, 1981, 2394;
41. T. Uyehara, Y. Kabasawa, T. Kato and T. Furuta, Tetrahedron Lett., 1985, 26, 2343;
42. T. Uyehara, Y. Kabasawa and T. Kato, Bull. Chem. Soc. Jpn., 1986, 59, 2521;
43. A. Gambacorta, M. Botta and S. Turchetta, Tetrahedron Lett., 1988, 29, 4846;
44. R. Baker, D. L. Selwood, C. J. Swain, N. M. H. Webster and J. Hirshfield, J. Chem. Soc., Perkin Trans. 1, 1988, 471;
45. A. F. Mateos, O. F. Barrueco and R. R. Gonzalez, Tetrahedron Lett., 1990, 31, 4343;
46. D. Schinzer, K. Ringe, R G. Jones and D. Doring, Tetrahedron Lett., 1995, 36, 4051.
47. M. Tori, H. Arbiyanti, Z. Taira and Y. Asakawa, Phytochemistry, 1993, 32, 335.
48. H. Tazaki, H. Soutome, T. Iwasaki, K. Nabeta and D. Arigoni, Chem. Commun., 1997, 1101.
49. A. Srikrishna and D. Vijaykumar, J. Chem. Soc., Perkin Trans. 1, 1999, 1265.
50. For a preliminary communication, see: A. Srikrishna and D. Vijaykumar, Tetrahedron Lett., 1998, 39, 4901.
51. S. Hannessian, Total Synthesis of Natural Products: The Chiron Approach, Pergamon Press, Oxford, 1983.
52. T. L. Ho, Enantioselective Synthesis. Natural Products from Chiral Terpenes, John Wiley, Chichester, 1992
53. G. Mehta, N. Krishnamurthy and S. R. Karra, J. Am. Chem. Soc., 1991, 113, 5765
54. A. A. Verstegen-Haaksma, B. J. M. Jansen and A. D. Groot, Tetrahedron, 1992, 48, 3121
55. V. N. Zhanbinskii, A. J. Minnaard, J. B. P. A. Wijnberg and A. D. Groot, J. Org. Chem., 1996, 61, 4022
56. P. M. F. M. Bastiaansen, J. B. P. A. Wijnberg and A. D. Groot, J. Org. Chem., 1996, 61, 4955 and references cited therein.
57. A. Srikrishna, P. Hemamalini and G. V. R. Sharma, Tetrahedron Lett., 1991, 32, 6609
58. J. Org. Chem., 1993, 58, 2509
59. A. Srikrishna and T. J. Reddy, Indian J. Chem., Sect. B, 1995, 34, 844
60. A. Srikrishna, S. Nagaraju, T. J. Reddy and S. Venkateswarlu, Pure Appl. Chem., 1996, 68, 699
61. A. Srikrishna, T. J. Reddy and S. Nagaraju, Tetrahedron Lett., 1996, 37, 1679
62. A. Srikrishna and R. Viswajanani, Tetrahedron Lett., 1996, 37, 2863
63. A. Srikrishna, T. J. Reddy and P. P. Kumar, Chem. Commun., 1996, 1369
64. A. Srikrishna and R. Viswajanani, Indian J. Chem., Sect. B, 1996, 35, 521
65. A. Srikrishna, D. Vijaykumar and T. J. Reddy, Tetrahedron, 1997, 53, 1439
66. A. Srikrishna and S. Danieldoss, J. Org. Chem., 1997, 62, 7863
67. A. Srikrishna and T. J. Reddy, J. Chem. Soc., Perkin Trans. 1, 1997, 3293
68. A. Srikrishna, P. P. Kumar and T. J. Reddy, Tetrahedron Lett., 1998, 39, 5815
69. A. Srikrishna and T. J. Reddy, J. Chem. Soc., Perkin Trans. 1, 1998, 2137
70. A. Srikrishna and S. J. Gharpure, Chem. Commun., 1998, 1589
71. A. Srikrishna and T. J. Reddy, Tetrahedron, 1998, 54, 11517
72. A. Srikrishna, T. J. Reddy and P. P. Kumar, J. Chem. Soc., Perkin Trans. 1, 1998, 3143
73. A. Srikrishna and S. J. Gharpure, Tetrahedron Lett., 1999, 40, 1035
74. A. Srikrishna and C. Dinesh, Indian J. Chem., Sect. B, 1999, 38, 1151
75. A. Srikrishna, S. J. Gharpure and P. P. Kumar, Tetrahedron Lett., 2000, 41, 3177
76. A. Srikrishna and C. Dinesh, Indian J. Chem., Sect. B, 2000, 39, in the press
77. A. Srikrishna, K. Anebouselvy and T. J. Reddy, Tetrahedron Lett., 2000, 41, in the press.
78. J.-P. Gesson, J.-C. Jaquesy and B. Renoux, Tetrahedron Lett., 1986, 27, 4461.
79. G. Buchi and B. Egger, J. Org. Chem., 1971, 36, 2021
80. A. Srikrishna and P. Hemamalini, Indian J. Chem. Sect. B, 1990, 29, 152
81. A. Srikrishna, G. V. R. Sharma, S. Danieldoss and P. Hemamalini, J. Chem. Soc., Perkin Trans. 1, 1996, 1305.
82. Y.-D. Wu, K. N. Houk, J. Florez and B. M. Trost, J. Org. Chem., 1991, 56, 3656
83. L. Garver, P. van Eikeren and J. E. Byrd, J. Org. Chem., 1976, 41, 2773.
84. L. Claisen, Ber. Dtsch. Chem. Ges., 1912, 45, 3157
85. W. S. Johnson, L. Werthemann, W. R. Bartlett, T. J. Brocksom, T.-t. Li, D. J. Faulkner and M. R. Petersen, J. Am. Chem. Soc., 1970, 92, 741
86. W. S. Johnson, T. J. Brocksom, P. Loew, D. H. Rich, L. Werthemann, R. A. Arnold, T.-t. Li and D. J. Faulkner, J. Am. Chem. Soc., 1970, 92, 4463.
87. G. Stork and J. Ficini, J. Am. Chem. Soc., 1961, 83, 4678
88. S. D. Burke and P. A. Grieco, Org. React., 1979, 26, 361
89. L. N. Mander, Synlett, 1991, 134;
90. A. Padwa and K. E. Krumpe, Tetrahedron, 1992, 48, 5385.
91. T. Norin, Acta Chem. Scand., 1963, 17, 738
92. W. G. Dauben and E. J. Deviny, J. Org. Chem., 1966, 31, 3794
93. W. G. Dauben and R. E. Wolf, J. Org. Chem., 1970, 35, 374
94. W. G. Dauben and R. E. Wolf, J. Org. Chem., 1970, 35, 2361
95. T. Norin, Acta Chem. Scand., 1965, 19, 1289;
96. A. Srikrishna, K. Krishnan and C. V. Yelamaggad, Tetrahedron, 1992, 48, 9725.
97. S. L. Schreiber and W.-F. Liew, Tetrahedron Lett., 1983, 24, 2363
98. R. Criegee, Ber. Dtsch. Chem. Ges., 1944, 77, 722.
99. For a general write-up on experimentation and instrumentation see ref. 8.
100. A. Srikrishna and S. J. Gharpure, Synlett., 2000, in the press.