Approaches to the Synthesis of Masked P-Quinone Methides. Applications to the Total Synthesis of (±)-Cherylline

Journal of the American Chemical Society

Volumn 100, Issue 5, 1978, Pages 1548-1557

  Hart, David J ^a   Cain, Paul A ^a   Evans, David A ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHERYLLINE; DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; INFRARED SPECTROMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; QUINONE METHIDE; THEORETICAL STUDY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0017802788     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00473a037     Document Type: Article

References (80)

1. For a review of the early quinone methide literature see A. B. Turner, Q. Rev., Chem. Soc., 18, 347 (1964).
2. For a review discussing the occurrence and chemistry of natural quinone methides see A. B. Turner, Fortschr. Chem. Org. Naturst., 24, 288 (1966).
3. For a more recent account of o-quinone methide literature see W. R. Schleigh, Eastman Org. Chem. Bull., 43, 1 (1971).
4. K. S. Brown, Chem. Soc. Rev., 4, 263 (1975);
5. K. S. Brown and U. Weiss, Tetrahedron Lett., 3501 (1971);
6. K. S. Brown and P. M. Balker, Tetrahedron Lett., 3505(1971).
7. W. D. Ollis and I. O. Sutherland in “Chemistry of Natural Phenolic Compounds”, W. D. Ollis, Ed., Permagon Press, Oxford, 1961, p 84.
8. K. Freudenberg, Fortschr. Chem. Org. Naturst., 20, 41 (1962);
9. A. I. Scott, O. Rev., Chem. Soc., 19, 1 (1965);
10. B. Johansson and G. E. Miksche, Acta Chem. Scand., 26, 289 (1972), and references cited therein.
11. R. J. Parry and J. M. Schwab, J. Am. Chem. Soc., 97, 2555 (1975).
12. M. Shamma and C. D. Jones, J. Am. Chem. Soc., 92, 4943 (1970);
13. M. Shamma and J. F. Nugent, Tetrahedron Lett., 2625 (1970).
14. M. A. Schwartz and S. W. Scott, J. Org. Chem., 36, 1827 (1971).
15. D. W. Brown, S, F. Dyke, G. Hardy, Tetrahedron Lett., 1515 (1969).
16. A. J. Lin, C. W. Shansky, and A. C. Sartorelli, J. Med. Chem., 17, 558 (1974). and references cited therein.
17. See H. V. Wagner and R. Gompper in “The Chemistry of Quinoid Compounds”, Part II, S. Patai, Ed., Wiley, New York, N. Y., 1974, pp 1145-1179.
18. H. E. Zimmerman and H. Craft, Tetrahedron Lett., 2131 (1964);
19. D. Bryce-Smith, G. I. Fray, and A. Gilbert, Part II., 2137 (1964);
20. J. L. Chitwood, P. G. Gott, J. J. Krutak, and J. C. Martin, J. Org. Chem., 36, 2216 (1971);
21. W. W. Sullivan, D, Ullman, and H. Shechter, Tetrahedron Lett., 457 (1969);
22. J. Parrick, Can. J. Chem., 42, 190 (1964);
23. H. J. Bestmann and H. J. Lang, Tetrahedron Lett., 2101 (1969);
24. J. Ficini and A. Krief, Part II, 2497 (1967);
25. M. E. Kuehne and H. Linde, J. Org. Chem., 32, 4031 (1972);
26. A. Mosterd and H. J. T. Boss, Recl. Trav. Chim. Pays-Bas, 94, 220 (1975).
27. D. A. Evans and J. M. Hoffman, J. Am. Chem. Soc., 98, 1983 (1976).
28. D. A. Evans, J. M. Hoffman, and L. K. Truesdale, J. Am. Chem. Soc., 95, 5822 (1973);
29. D. A. Evans and R. Y. Wong, J. Org. Chem., 42, 350 (1977), and references cited therein.
30. For isolation and identification see A. Brossi, G. Grethe, S. Teitel, W. C. Wildman, and D. T. Bailey, J. Org. Chem., 35, 1100 (1970).
31. M. A. Schwartz and S. W. Scott, J. Org. Chem., 36, 1827 (1971).
32. T. Kametani, K. Takahashi, and C. V. Loc, Tetrahedron, 31, 235 (1975).
33. For a more recent account of o-quinone methide literature see W. R. Schleigh, Eastman Org. Chem. Bull., 43, 1 (1971).
34. A. Brossi and S. Teitel, Tetrahedron Lett., 417 (1970);
35. A. Brossi and S. Teitel, J. Org. Chem., 35, 3559 (1970).
36. P. F. Hudrlik, D. Peterson, and D. Chou, Synth. Commun., 5, 359 (1975), and references cited therein.
37. R. A. Ruden, J. Org. Chem., 39, 3607 (1974).
38. S. L. Hartzell and M. W. Rathke, Tetrahedron Lett., 2737, 2757 (1976), and references cited therein. Also see ref 16.
39. R. Y. Wong, University of California, Los Angeles, 1976.
40. thallium(III) nitrate: A. M. McKillop, D. H. Perry, M. Edwards, S. Antus, L. Farkas, M. Nógrádi, and E. C. Taylor, J. Org Chem., 41, 282 (1976).
41. Copper(ll) amine complexes: D. G. Hewitt, J. Chem. Soc., C, 2967 (1971).
42. Ceric ammonium nitrate and N-bromosuccinimide: W. Durchheimer and L. A. Cohen, Biochemistry, 3, 1948 (1964).
43. Silver oxide, DDQ, and manganese dioxide: I. G. C. Coutts, D. J. Humphreys, and K. Schofield, J. Chem. Soc. C, 1982 (1969).
44. A. Nilsson, A. Ronlan, and V. D. Parker, Tetrahedron Lett., 1107 (1975).
45. N. C. Weinberg and E. A. Brown, J. Org. Chem., 31, 4054 (1966);
46. J. E. Heller, A. S. Dreiding, B. R. O'Connor, H. E. Simmons, G. L. Buchanan, R. A. Raphael, and R. Taylor, Helv. Chim. Acta, 56, 272 (1973);
47. G. L. Buchanan, R. A. Raphael, and R. Taylor, J. Chem. Soc., Perkin Trans. 1, 373 (1973);
48. P. Margaretha and P. Tissot, Helv. Chim. Acta, 58, 933 (1975);
49. B. Belleau and N. L. Weinberg, J. Am. Chem. Soc., 85, 2525 (1963);
50. J. S. Swenton, M. J. Manning, and P. W. Raynolds, J. Am. Chem. Soc., 98, 5008 (1976).
51. This reduction most likely proceeds via rearrangement to 11a or the corresponding trifluoroacetate and subsequent reduction. For a recent review on ionic hydrogenations see D. N. Kursanov, Z. N. Parnes, and N. M. Loim, Synthesis, 633 (1974).
52. R. F. Borch, M. D. Bernstein, and H. D. Durst, J. Am. Chem. Soc., 93, 2897 (1971);
53. G. Grethe, H. L. Lee, M. Uskoković, and A. Brossi, J. Org. Chem., 33, 491 (1968).
54. For a relevant study see A. H. Lewin, M. Frucht, K. V. J. Chen, E. Benedetti, and B. DiBlasio, Tetrahedron, 31, 207 (1975).
55. For a recent review on the synthesis and rearrangement of spirodienones see R. S. Ward, Chem. Br., 444 (1973).
56. B. Miller in “Mechanisms of Molecular Migrations”, Vol. 1, B. S. Thyagarajan, Ed., Wiley-Interscience, New York, N. Y., 1968, p 247;
57. I. Saito, Y. Chujo, H. Shimazu, M. Yamune, T. Matsuura, and H. J. Cahnmann, J. Am. Chem. Soc., 97, 5272 (1975).
58. A. H. Jackson and J. A. Martin, J. Chem. Soc. C, 2222 (1966);
59. T. Kametani, F. Satoh, H. Yagi, and K. Fukimoto, Chem. Commun., 1103 (1967)
60. S. M. Kupchan, O. P. Dhingra, and C. Kim, J. Org. Chem., 41, 4049 (1976).
61. Ar1-5 participation was originally observed by R. Baird and S. Winstein, J. Am. Chem. Soc., 84, 788 (1962), and references cited therein.
62. T. J. Schwan, G. S. Lougheed, and S. E. Burrows, J. Heterocycl. Chem., 11, 807 (1974);
63. D. L. Trepanier and S. Sunder, J. Med. Chem., 16, 342 (1973).
64. R. N. Mirrington and G. I. Feutrill, Aust. J. Chem., 25, 1719 (1972).
65. For another procedure for selective nucleophilic aryl ether cleavage see C. Hansson and B. Wickberg, Synthesis, 191 (1976).
66. For a review on selective O-demethylations of isoquinolines see S. Teitel and A. Brossi, Heterocycles, 1, 73 (1973).
67. A pure sample of 27 was inadvertently obtained in low yield when 20b was subjected to an excess of lithium aluminum hydride at elevated temperatures for a long time (see Experimental Section).
68. B. Umezawa, O. Hoshino, Y. Terayama, K. Ohyama, Y. Yamanashi, T. Inove, and T. Toshioka, Chem. Pharm. Bull., 19, 2138 (1971);
69. B. Umezawa, O. Hoshino, and Y. Terayama, Chem. Pharm. Bull., 16, 180 (1968).
70. J. C. Martin and R. J. Arhart, J. Am. Chem. Soc., 93, 4327 (1971); 94, 5003 (1972);
71. J. C. Martin, J. A. Franz, and R. J. Arhart, J. Am. Chem. Soc., 98, 4604 (1974).
72. E. E. Sohweizer and R. D. Bach, J. Org. Chem., 29, 1746 (1964);
73. E. E. Schweizer, L. D. Smucker, and R. J. Votral, J. Org. Chem., 31, 467 (1966).
74. C. Kaiser, R. G. Pendleton, and P. E. Setler, Chem. Abstr., 86, 189474p (1977).
75. via π-bonded organometallics: M. F. Semmelhack and G. Clark, J. Am. Chem. Soc., 99, 1675 (1977)
76. via σ-bonded arylnickel complexes: M. F. Semmelhack, R. D. Stauffer, and T. D. Rogerson. Tetrahedron Lett., 4519 (1973).
77. via electron-deficient aryl halides: J. F. Bunnett, Q. Rev., Chem. Soc., 12, 1 (1958).
78. via photostimulated SRN1 reaction: J. F. Bunnett and J. E. Sundberg, J. Org. Chem., 41, 1702 (1976)
79. via cyclohexadienyliron tricarbonyl cations: R. E. Ireland, G. G. Brown, R. H. Stanford, and T. C. McKenzie, J. Org. Chem., 39, 51 (1974).
80. For a related procedure see H. Bruderer and A. Brossi, Helv. Chim. Acta, 48, 1945 (1965).