Asymmetric synthesis of chiral chromans

Tetrahedron

Volumn 65, Issue 20, 2009, Pages 3931-3952

  Shen, Hong C ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL CHROMAN; CHROMAN DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ALLYLATION; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; DIHYDROXYLATION; EPOXIDATION; HYDROGENATION; PRIORITY JOURNAL; REVIEW; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 64349094226     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.002     Document Type: Review

References (114)

1. In: Machlin L.J. (Ed). α-Tocopherol (1980), Marcel Dekker, New York, NY
2. Terao K., and Niki E. J. Free Rad Biol. Med. 2 (1986) 193
3. Grisar J.M., Petty M.A., Bolkenius F.N., Dow J., Wagner J., Wagner E.R., Haegele K.D., and Jong W.D. J. Med. Chem. 34 (1991) 257
4. Smith E., Pucci L.A., and Bywater L.G. Science 115 (1952) 520
5. Shanbhag X.N., Mesta C.K., Maheshwari M.C., and Bhattacharyya S.C. Tetrahedron 21 (1965) 3591
6. De Cree J., Geukens H., Leempoels J., and Verhaegen H. Drug Dev. Res. 8 (1986) 109
7. Van de Water A., Janssen W., Van Nueten J., Xhonneux R., De Cree J., Verhaegen H., Reneman R.S., and Janssen P.A.J. J. Cardiovasc. Pharmacol. 11 (1988) 552
8. Evans J.M., and Stemp B. Chem. Br. (1991) 439
9. Bosch R.F., Gaspo R., Busch A.E., Lang H.J., Li G.R., and Nattel S. Cardivasc. Res. 38 (1988) 441
10. Valsamakis G., and Kumar S. Exp. Opin. Pharmacother. 1 (2000) 1413 and references therein
11. Isabashi K. J. Antibiot., Ser. A 15 (1962) 161
12. Kashiwada Y., Yamazaki K., Ikeshiro Y., Yamagishi T., Fujioka T., Mihashi K., Mizuki K., Cosentino L.M., Fowke K., Morris-Natschke S.L., and Lee K.-H. Tetrahedron 57 (2001) 1559
13. Kashman Y., Gustafson K.R., Fuller R.W., Cardellina II J.H., McMahon J.B., Currens M.J., Buckhiet Jr. R.W., Hughes S.H., Cragg G.M., and Boyd M.R. J. Med. Chem. 35 (1992) 273
14. Taylor P.B., Culp J.S., Debouck C., Johnson R.K., Patil A.D., Woolf D.J., Brooks I., and Hertzberg R.P. J. Biol. Chem. 269 (1994) 632
15. Minagawa K., Kouzuki S., Yoshimoto J., Kawamura Y., Tani H., Iwata T., Terui Y., Nakai H., Yagi S., Hattori N., Fujiwara T., and Kamigauchi T. J. Antibiot. 55 (2002) 155
16. Minagawa K., Kouzuki S., and Kamigauchi T. J. Antibiot. 55 (2002) 165
17. Roll D.M., Manning J.K., and Carter G.T. J. Antibiot. 51 (1998) 635
18. Pistelli L., Noccioli C., Appendino G., Bianchi F., Sterner O., and Ballero M. Phytochemistry 64 (2003) 595
19. Sankaran M.S., and Prasad M.R.N. Contraception 9 (1974) 279
20. Morito K., Hirose T., Kinjo J., Hirakawa T., Okawa M., Nohara T., Ogawa S., Inoue S., Muramatsu M., and Masamune Y. Biol. Pharm. Bull. 24 (2001) 351
21. Schmitt E., Dekant W., and Sopper H. Toxicol. In Vitro 15 (2001) 433
22. Weyant M.J., Carothers A.M., Dannenberg A.J., and Bertagnolli M.M. Cancer Res. 61 (2001) 118
23. Chyu K.Y., Babbidge S.M., Zhao X., Dandillaya R., Rietveld A.G., Yano J., Dimayuga P., Cercek B., and Shah P.K. Circulation 109 (2004) 2448
24. Barrero A.F., Alvarez-Manzaneda E.J., and Chahboun R. Tetrahedron 55 (1999) 15181
25. Ward A., and Holmes B. Drugs 30 (1985) 127
26. Stouter R.W. Anal. Profiles Drug Subs. 10 (1981) 499
27. Lambert D.M., and Fowler C.J. J. Med. Chem. 48 (2005) 5059
28. Comoy C., Marot C., Podona T., Baudin M.L., Morin-Allory L., Guillaumet G., Peiffer B., Caignard D.H., Renard P., Rettori M.C., Adam G., and Guardiola-Lemaître B. J. Med. Chem. 39 (1996) 4285
29. Judzewitsch R.G., Jaspan J.B., Polonsky K.S., Weinberg C.R., Halter J.B., Halar E., Pfeifer M.A., Vukadinovic C., Bernstein L., Schneider M., Liang K.Y., Gabbay K.H., Rubenstein A.H., and Porte D. N. Engl. J. Med. 308 (1983) 119
30. For other reviews related to chromans and chromenes, see:
31. Tang Y., Oppenheimer J., Song Z., You L., Zhang X., and Hsung R.P. Tetrahedron 62 (2006) 10785
32. Beaudry C.M., Malerich J.P., and Trauner D. Chem. Rev. 105 (2005) 4757
33. Hsung R.P., Kurdyumov A.V., and Sydorenko N. Eur. J. Org. Chem. (2005) 23
34. Pámies O., and Bäckvall J.-E. Chem. Rev. 103 (2003) 3247
35. For a recent review, see:. Keith J.M., Larrow J.F., and Jacobsen E.N. Adv. Synth. Catal. 1 (2001) 5
36. For reviews:
37. Schoffers E., Golebiowski A., and Johnson C.R. Tetrahedron 52 (1996) 3769
38. Otera J. Chem. Rev. 93 (1993) 1449
39. In: Drauz K., and Waldman H. (Eds). Enzymes Catalysis in Organic Synthesis Vols. 1 and 2 (1995), VCH Verlagsgesellschaft mbH, Weinheim
40. Rao A.V.R., Gaitonde A.S., Prakash K.R.C., and Rao S.P. Tetrahedron Lett. 35 (1994) 6347
41. Brown H.C., and Bhat K.S. J. Am. Chem. Soc. 108 (1986) 5919
42. Deshpande P.P., and Baker D.C. Synthesis (1995) 630
43. Mikoshiba H., Midami K., and Nakai T. Synlett (2001) 989
44. Kurdyumov A.V., and Hsung R.P. J. Am. Chem. Soc. 128 (2006) 6272
45. Barrero A.F., Alvarez-Manzaneda E.J., and Chahboun R. Tetrahedron Lett. 38 (1997) 2325
46. Barrero A.F., Alvarez-Manzaneda E.J., Chahboun R., Cotés M., and Armstrong V. Tetrahedron 55 (1999) 15181
47. Deng W.-P., Zhong M., Guo X.-C., and Kende A.S. J. Org. Chem. 68 (2003) 7422
48. For a similar approach that leads to (+)-chloropuupehenone:. Hua D.H., Huang X., Chen Y., Battina S.K., Tamura M., Noh S.K., Koo S.I., Namatame I., Tomoda H., Perchellet E.M., and Perchellet J.-P. J. Org. Chem. 69 (2004) 6065
49. For a similar approach to the tetracyclic ABCD ring system of kampanols:. Iwasaki K., Nakatani M., Inoue M., and Katoh T. Tetrahedron 59 (2003) 8763
50. Song Y., Hwang S., Gong P., Kim D., and Kim S. Org. Lett. 10 (2008) 269
51. Lee T., and Kim S. Tetrahedron: Asymmetry 14 (2003) 1951
52. Lipinski C.A., Aldinger C.E., Beyer T.A., Bordner J., Burdi D.E., Bussolotti D.L., Inskeep P.B., and Siegel T.W. J. Med. Chem. 35 (1992) 2169
53. Nakamura M., Suzuki A., Nakatani M., Fuchikami T., Inoue M., and Katoh T. Tetrahedron Lett. 43 (2002) 6929
54. Kawano H., Itoh M., Katoh T., and Terashima S. Tetrahedron Lett. 38 (1997) 7769
55. Nakatani M., Nakamura M., Suzuki A., Inoue M., and Katoh T. Org. Lett. 4 (2002) 4483
56. Cohen N., Lopresti R.J., and Saucy G. J. Am. Chem. Soc. 101 (1979) 6710
57. Mori K. Tetrahedron 31 (1975) 1381
58. Holmberg P., Tedenborg L., Rosqvist S., and Johansson A.M. Bioorg. Med. Chem. Lett. 15 (2005) 747
59. Mizuguchi E., Suzuki T., and Achiwa K. Synlett (1994) 929
60. Kawasaki M., Kakuda H., Goto M., Kawabata S., and Kometani T. Tetrahedron: Asymmetry 14 (2003) 1529
61. Rein C., Demel P., Outten R.A., Netscher T., and Breit B. Angew. Chem., Int. Ed. 46 (2007) 8670
62. Kingsbury J.S., Harrity J.P.A., Bonitatebus Jr. P.J., and Hoveyda A.H. J. Am. Chem. Soc. 121 (1999) 791
63. Johannes C.W., Visser M.S., Weatherhead G.S., and Hoveyda A.H. J. Am. Chem. Soc. 120 (1998) 8340
64. Harrity J.P.A., La D.S., Cefalo D.R., Visser M.S., and Hoveyda A.H. J. Am. Chem. Soc. 120 (1998) 2343
65. Palucki M., and Yasuda N. Tetrahedron Lett. 46 (2005) 987
66. Trost B.M., and McEachern E.J. J. Am. Chem. Soc. 121 (1999) 8649
67. Torraca K.E., Huang X., Parrish C.A., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 10770
68. Harada T., Hayashiya T., Wada I., Iwa-ake N., and Oku A. J. Am. Chem. Soc. 109 (1987) 527
69. Chênevert R., and Courchesne G. Tetrahedron Lett. 43 (2002) 7971
70. Mizuguchi E., Suzuki T., and Achiwa K. Synlett (1996) 743
71. Nozawa M., Takahashi K., Kato K., and Akita H. Chem. Pharm. Bull. 48 (2000) 272
72. Solladie G., and Moine G. J. Am. Chem. Soc. 106 (1984) 6097
73. Sakito Y., and Suzukamo G. Tetrahedron Lett. 23 (1982) 4953
74. Hübscher J., and Barner R. Helv. Chim. Acta 73 (1990) 1068
75. Heemstra J.M., Kerrigan S.A., Doerge D.R., Helferich W.G., and Boulanger W.A. Org. Lett. 8 (2006) 5441
76. Stocker A., Ruttimann A., and Woggon W.-D. Helv. Chim. Acta 76 (1993) 1729
77. Grütter C., Alonso E., Chougnet A., and Woggon W.-D. Angew. Chem., Int. Ed. 45 (2006) 1126
78. Korthals K.A., and Wulff W.D. J. Am. Chem. Soc. 130 (2008) 2898
79. Gassman P.G., and Amick D.R. J. Am. Chem. Soc. 100 (1978) 7611
80. Inoue S., Ikeda H., Sato S., Horie K., Ota T., Miyamoto O., and Sato K. J. Org. Chem. 52 (1987) 5495
81. Mizuguchi E., and Achiwa K. Synlett (1995) 1255
82. Goujon J.-Y., Duval A., and Kirschleger B. J. Chem. Soc., Perkin Trans. 1 (2002) 496
83. Chandrasekhar S., and Reddy M.V. Tetrahedron 56 (2000) 6339
84. Mente N.R., Neighbors J.D., and Wiemer D.F. J. Org. Chem. 73 (2008) 7963
85. Shi Y. Acc. Chem. Res. 37 (2004) 488
86. Zhao M.-X., and Shi Y. J. Org. Chem. 71 (2006) 5377
87. Chapelat J., Buss A., Chougnet A., and Woggon W.-D. Org. Lett. 10 (2008) 5123
88. Baldwin J. J. Chem. Soc., Chem. Commun. (1976) 734
89. Marcos R., Rodríguez-Escrich C., Herrerías C.I., and Pericàs M.I. J. Am. Chem. Soc. 130 (2008) 16838
90. Kolb H.C., VanNieuwenhze M.S., and Sharpless B.K. Chem. Rev. 94 (1994) 2483
91. Tietze L.F., and Gorlitzer J. Synthesis (1996) 877
92. Jew S., Lim D., Bae S., Kim H., Kim J., Lee J., and Park H. Tetrahedron: Asymmetry 13 (2002) 715
93. Khupse R.S., and Erhardt P.W. Org. Lett. 10 (2008) 5007
94. Kitamura M., Suga S., Kawai K., and Noyori R. J. Am. Chem. Soc. 101 (1986) 6071
95. Uozumi Y., Kato K., and Hayashi T. J. Am. Chem. Soc. 119 (1997) 5063
96. Tietze L.F., Sommer K.M., Zinngrebe J., and Stecker F. Angew. Chem., Int. Ed. 43 (2004) 257
97. Tietze L.F., Stecker F., Zinngrebe J., and Sommer K.M. Chem.-Eur. J. 12 (2006) 8770
98. Trost B.M., and Toste D.F. J. Am. Chem. Soc. 120 (1998) 9074
99. Mizuguchi E., and Achiwa K. Chem. Pharm. Bull. 45 (1997) 1209
100. Labrosse J.-R., Poncet C., Lhoste P., and Sinou D. Tetrahedron: Asymmetry 10 (1999) 1069
101. Trost B.M., Shen H.C., and Surviet J.P. Angew. Chem., Int. Ed. 42 (2003) 3943
102. Trost B.M., Shen H.C., and Surivet J.-P. J. Am. Chem. Soc. 125 (2003) 9276
103. Tian X., and Rychnovsky S.D. Org. Lett. 9 (2007) 4955
104. Ishihara K., Nakamura S., and Yamamoto H. J. Am. Chem. Soc. 121 (1999) 4906
105. Nakamura S., Ishihara K., and Yamamoto H. J. Am. Chem. Soc. 122 (2000) 8131
106. Kumazawa K., Ishihara K., and Yamamoto H. Org. Lett. 6 (2004) 2551
107. Ishibashi H., Ishihara K., and Yamamoto H. J. Am. Chem. Soc. 126 (2004) 11122
108. Liu K., Chougnet A., and Woggon W.-D. Angew. Chem., Int. Ed. 47 (2008) 5827
109. Fukamizu K., Miyake Y., and Nishibayashi Y. J. Am. Chem. Soc. 130 (2008) 10498
110. Daini M., Yoshikawa M., Inada Y., Uemura S., Sakata K., Kanao K., Miyake Y., and Nishibayashi Y. Organometallics 27 (2008) 2046
111. Chung, Y.K.; Fu, G.C. Angew. Chem., Int. Ed., in press.
112. Nicolaou K.C., Reingruber R., Sarlah D., and Bräse S. J. Am. Chem. Soc. 131 (2009) 2086
113. Beeson T.D., Mastracchio A., Hong J.B., Ashton K., and MacMillan D.W.C. Science 316 (2007) 582
114. Wu X., Zhou J., and Snider B.B. Angew. Chem., Int. Ed. 48 (2009) 1283